CN108330154B - 酯酶EstP00714在催化拆分外消旋乙酸芳樟酯得到(S)-芳樟醇中的应用 - Google Patents
酯酶EstP00714在催化拆分外消旋乙酸芳樟酯得到(S)-芳樟醇中的应用 Download PDFInfo
- Publication number
- CN108330154B CN108330154B CN201810078725.0A CN201810078725A CN108330154B CN 108330154 B CN108330154 B CN 108330154B CN 201810078725 A CN201810078725 A CN 201810078725A CN 108330154 B CN108330154 B CN 108330154B
- Authority
- CN
- China
- Prior art keywords
- estp00714
- esterase
- racemic
- linalyl acetate
- linalool
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- UWKAYLJWKGQEPM-LBPRGKRZSA-N linalyl acetate Chemical compound CC(C)=CCC[C@](C)(C=C)OC(C)=O UWKAYLJWKGQEPM-LBPRGKRZSA-N 0.000 title claims abstract description 94
- 108090000371 Esterases Proteins 0.000 title claims abstract description 62
- UWKAYLJWKGQEPM-UHFFFAOYSA-N linalool acetate Natural products CC(C)=CCCC(C)(C=C)OC(C)=O UWKAYLJWKGQEPM-UHFFFAOYSA-N 0.000 title claims abstract description 47
- CDOSHBSSFJOMGT-SNVBAGLBSA-N (S)-linalool Chemical compound CC(C)=CCC[C@](C)(O)C=C CDOSHBSSFJOMGT-SNVBAGLBSA-N 0.000 title claims abstract description 39
- 230000003197 catalytic effect Effects 0.000 title claims description 7
- 238000006243 chemical reaction Methods 0.000 claims abstract description 45
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 20
- 239000000758 substrate Substances 0.000 claims description 15
- 239000000872 buffer Substances 0.000 claims description 13
- 235000019832 sodium triphosphate Nutrition 0.000 claims description 10
- 239000003960 organic solvent Substances 0.000 claims description 9
- 239000004094 surface-active agent Substances 0.000 claims description 8
- 230000035484 reaction time Effects 0.000 claims description 5
- 238000006555 catalytic reaction Methods 0.000 claims 2
- 239000013543 active substance Substances 0.000 claims 1
- 125000003275 alpha amino acid group Chemical group 0.000 claims 1
- 238000000926 separation method Methods 0.000 abstract description 5
- 239000012847 fine chemical Substances 0.000 abstract description 3
- 239000003054 catalyst Substances 0.000 abstract description 2
- 239000002537 cosmetic Substances 0.000 abstract description 2
- 239000000126 substance Substances 0.000 abstract description 2
- 108090000790 Enzymes Proteins 0.000 description 16
- 102000004190 Enzymes Human genes 0.000 description 16
- 230000000694 effects Effects 0.000 description 14
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 description 9
- 239000000843 powder Substances 0.000 description 8
- CDOSHBSSFJOMGT-JTQLQIEISA-N (R)-linalool Natural products CC(C)=CCC[C@@](C)(O)C=C CDOSHBSSFJOMGT-JTQLQIEISA-N 0.000 description 5
- 241000704896 Pseudonocardia antitumoralis Species 0.000 description 5
- 230000007423 decrease Effects 0.000 description 5
- 108090000623 proteins and genes Proteins 0.000 description 5
- 150000001413 amino acids Chemical group 0.000 description 4
- 238000001514 detection method Methods 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- YBAFDPFAUTYYRW-UHFFFAOYSA-N N-L-alpha-glutamyl-L-leucine Natural products CC(C)CC(C(O)=O)NC(=O)C(N)CCC(O)=O YBAFDPFAUTYYRW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 239000002773 nucleotide Substances 0.000 description 3
- 125000003729 nucleotide group Chemical group 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000001490 (3R)-3,7-dimethylocta-1,6-dien-3-ol Substances 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- HNAUFGBKJLTWQE-IFFSRLJSSA-N Gln-Val-Thr Chemical compound C[C@H]([C@@H](C(=O)O)NC(=O)[C@H](C(C)C)NC(=O)[C@H](CCC(=O)N)N)O HNAUFGBKJLTWQE-IFFSRLJSSA-N 0.000 description 2
- CCBIBMKQNXHNIN-ZETCQYMHSA-N Gly-Leu-Gly Chemical compound NCC(=O)N[C@@H](CC(C)C)C(=O)NCC(O)=O CCBIBMKQNXHNIN-ZETCQYMHSA-N 0.000 description 2
- 108010079364 N-glycylalanine Proteins 0.000 description 2
- 241000589516 Pseudomonas Species 0.000 description 2
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 2
- 108010013835 arginine glutamate Proteins 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- VPZXBVLAVMBEQI-UHFFFAOYSA-N glycyl-DL-alpha-alanine Natural products OC(=O)C(C)NC(=O)CN VPZXBVLAVMBEQI-UHFFFAOYSA-N 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 229930007744 linalool Natural products 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 238000005809 transesterification reaction Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 description 1
- XVZCXCTYGHPNEM-IHRRRGAJSA-N (2s)-1-[(2s)-2-[[(2s)-2-amino-4-methylpentanoyl]amino]-4-methylpentanoyl]pyrrolidine-2-carboxylic acid Chemical compound CC(C)C[C@H](N)C(=O)N[C@@H](CC(C)C)C(=O)N1CCC[C@H]1C(O)=O XVZCXCTYGHPNEM-IHRRRGAJSA-N 0.000 description 1
- ZCPBEAHAVUJKAE-UHTWSYAYSA-N (2s)-2-[[(2s)-2-[[(2r)-2-[(2-aminoacetyl)amino]-3-phenylpropanoyl]amino]propanoyl]amino]butanedioic acid Chemical compound OC(=O)C[C@@H](C(O)=O)NC(=O)[C@H](C)NC(=O)[C@H](NC(=O)CN)CC1=CC=CC=C1 ZCPBEAHAVUJKAE-UHTWSYAYSA-N 0.000 description 1
- YLTKNGYYPIWKHZ-ACZMJKKPSA-N Ala-Ala-Glu Chemical compound C[C@H](N)C(=O)N[C@@H](C)C(=O)N[C@H](C(O)=O)CCC(O)=O YLTKNGYYPIWKHZ-ACZMJKKPSA-N 0.000 description 1
- UCIYCBSJBQGDGM-LPEHRKFASA-N Ala-Arg-Pro Chemical compound C[C@@H](C(=O)N[C@@H](CCCN=C(N)N)C(=O)N1CCC[C@@H]1C(=O)O)N UCIYCBSJBQGDGM-LPEHRKFASA-N 0.000 description 1
- JAMAWBXXKFGFGX-KZVJFYERSA-N Ala-Arg-Thr Chemical compound [H]N[C@@H](C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H]([C@@H](C)O)C(O)=O JAMAWBXXKFGFGX-KZVJFYERSA-N 0.000 description 1
- WYPUMLRSQMKIJU-BPNCWPANSA-N Ala-Arg-Tyr Chemical compound [H]N[C@@H](C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC1=CC=C(O)C=C1)C(O)=O WYPUMLRSQMKIJU-BPNCWPANSA-N 0.000 description 1
- LSLIRHLIUDVNBN-CIUDSAMLSA-N Ala-Asp-Lys Chemical compound C[C@H](N)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@H](C(O)=O)CCCCN LSLIRHLIUDVNBN-CIUDSAMLSA-N 0.000 description 1
- LGFCAXJBAZESCF-ACZMJKKPSA-N Ala-Gln-Ala Chemical compound [H]N[C@@H](C)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](C)C(O)=O LGFCAXJBAZESCF-ACZMJKKPSA-N 0.000 description 1
- PCIFXPRIFWKWLK-YUMQZZPRSA-N Ala-Gly-Leu Chemical compound CC(C)C[C@@H](C(O)=O)NC(=O)CNC(=O)[C@H](C)N PCIFXPRIFWKWLK-YUMQZZPRSA-N 0.000 description 1
- TZDNWXDLYFIFPT-BJDJZHNGSA-N Ala-Ile-Leu Chemical compound [H]N[C@@H](C)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC(C)C)C(O)=O TZDNWXDLYFIFPT-BJDJZHNGSA-N 0.000 description 1
- LXAARTARZJJCMB-CIQUZCHMSA-N Ala-Ile-Thr Chemical compound [H]N[C@@H](C)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)O)C(O)=O LXAARTARZJJCMB-CIQUZCHMSA-N 0.000 description 1
- LBYMZCVBOKYZNS-CIUDSAMLSA-N Ala-Leu-Asp Chemical compound [H]N[C@@H](C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(O)=O)C(O)=O LBYMZCVBOKYZNS-CIUDSAMLSA-N 0.000 description 1
- SUMYEVXWCAYLLJ-GUBZILKMSA-N Ala-Leu-Gln Chemical compound [H]N[C@@H](C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(O)=O SUMYEVXWCAYLLJ-GUBZILKMSA-N 0.000 description 1
- 108010011667 Ala-Phe-Ala Proteins 0.000 description 1
- XRUJOVRWNMBAAA-NHCYSSNCSA-N Ala-Phe-Ala Chemical compound OC(=O)[C@H](C)NC(=O)[C@@H](NC(=O)[C@@H](N)C)CC1=CC=CC=C1 XRUJOVRWNMBAAA-NHCYSSNCSA-N 0.000 description 1
- DHBKYZYFEXXUAK-ONGXEEELSA-N Ala-Phe-Gly Chemical compound OC(=O)CNC(=O)[C@@H](NC(=O)[C@@H](N)C)CC1=CC=CC=C1 DHBKYZYFEXXUAK-ONGXEEELSA-N 0.000 description 1
- CYBJZLQSUJEMAS-LFSVMHDDSA-N Ala-Phe-Thr Chemical compound C[C@H]([C@@H](C(=O)O)NC(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@H](C)N)O CYBJZLQSUJEMAS-LFSVMHDDSA-N 0.000 description 1
- JNLDTVRGXMSYJC-UVBJJODRSA-N Ala-Pro-Trp Chemical compound C[C@H](N)C(=O)N1CCC[C@H]1C(=O)N[C@@H](Cc1c[nH]c2ccccc12)C(O)=O JNLDTVRGXMSYJC-UVBJJODRSA-N 0.000 description 1
- YHBDGLZYNIARKJ-GUBZILKMSA-N Ala-Pro-Val Chemical compound CC(C)[C@@H](C(O)=O)NC(=O)[C@@H]1CCCN1C(=O)[C@H](C)N YHBDGLZYNIARKJ-GUBZILKMSA-N 0.000 description 1
- JJHBEVZAZXZREW-LFSVMHDDSA-N Ala-Thr-Phe Chemical compound C[C@@H](O)[C@H](NC(=O)[C@H](C)N)C(=O)N[C@@H](Cc1ccccc1)C(O)=O JJHBEVZAZXZREW-LFSVMHDDSA-N 0.000 description 1
- IYKVSFNGSWTTNZ-GUBZILKMSA-N Ala-Val-Arg Chemical compound C[C@H](N)C(=O)N[C@@H](C(C)C)C(=O)N[C@H](C(O)=O)CCCN=C(N)N IYKVSFNGSWTTNZ-GUBZILKMSA-N 0.000 description 1
- OMSKGWFGWCQFBD-KZVJFYERSA-N Ala-Val-Thr Chemical compound [H]N[C@@H](C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H]([C@@H](C)O)C(O)=O OMSKGWFGWCQFBD-KZVJFYERSA-N 0.000 description 1
- KWKQGHSSNHPGOW-BQBZGAKWSA-N Arg-Ala-Gly Chemical compound [H]N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](C)C(=O)NCC(O)=O KWKQGHSSNHPGOW-BQBZGAKWSA-N 0.000 description 1
- KMFPQTITXUKJOV-DCAQKATOSA-N Arg-Ser-Leu Chemical compound [H]N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(C)C)C(O)=O KMFPQTITXUKJOV-DCAQKATOSA-N 0.000 description 1
- GWNMUVANAWDZTI-YUMQZZPRSA-N Asn-Gly-His Chemical compound C1=C(NC=N1)C[C@@H](C(=O)O)NC(=O)CNC(=O)[C@H](CC(=O)N)N GWNMUVANAWDZTI-YUMQZZPRSA-N 0.000 description 1
- GIQCDTKOIPUDSG-GARJFASQSA-N Asn-Lys-Pro Chemical compound C1C[C@@H](N(C1)C(=O)[C@H](CCCCN)NC(=O)[C@H](CC(=O)N)N)C(=O)O GIQCDTKOIPUDSG-GARJFASQSA-N 0.000 description 1
- VCJCPARXDBEGNE-GUBZILKMSA-N Asn-Pro-Pro Chemical compound NC(=O)C[C@H](N)C(=O)N1CCC[C@H]1C(=O)N1[C@H](C(O)=O)CCC1 VCJCPARXDBEGNE-GUBZILKMSA-N 0.000 description 1
- NYLBGYLHBDFRHL-VEVYYDQMSA-N Asp-Arg-Thr Chemical compound [H]N[C@@H](CC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H]([C@@H](C)O)C(O)=O NYLBGYLHBDFRHL-VEVYYDQMSA-N 0.000 description 1
- WCFCYFDBMNFSPA-ACZMJKKPSA-N Asp-Asp-Glu Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@H](C(O)=O)CCC(O)=O WCFCYFDBMNFSPA-ACZMJKKPSA-N 0.000 description 1
- CSEJMKNZDCJYGJ-XHNCKOQMSA-N Asp-Gln-Pro Chemical compound C1C[C@@H](N(C1)C(=O)[C@H](CCC(=O)N)NC(=O)[C@H](CC(=O)O)N)C(=O)O CSEJMKNZDCJYGJ-XHNCKOQMSA-N 0.000 description 1
- YNCHFVRXEQFPBY-BQBZGAKWSA-N Asp-Gly-Arg Chemical compound OC(=O)C[C@H](N)C(=O)NCC(=O)N[C@H](C(O)=O)CCCN=C(N)N YNCHFVRXEQFPBY-BQBZGAKWSA-N 0.000 description 1
- HJZLUGQGJWXJCJ-CIUDSAMLSA-N Asp-Pro-Gln Chemical compound [H]N[C@@H](CC(O)=O)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CCC(N)=O)C(O)=O HJZLUGQGJWXJCJ-CIUDSAMLSA-N 0.000 description 1
- XWKBWZXGNXTDKY-ZKWXMUAHSA-N Asp-Val-Ala Chemical compound OC(=O)[C@H](C)NC(=O)[C@H](C(C)C)NC(=O)[C@@H](N)CC(O)=O XWKBWZXGNXTDKY-ZKWXMUAHSA-N 0.000 description 1
- ZLHPWFSAUJEEAN-KBIXCLLPSA-N Cys-Ile-Gln Chemical compound CC[C@H](C)[C@@H](C(=O)N[C@@H](CCC(=O)N)C(=O)O)NC(=O)[C@H](CS)N ZLHPWFSAUJEEAN-KBIXCLLPSA-N 0.000 description 1
- HSAWNMMTZCLTPY-DCAQKATOSA-N Cys-Met-Leu Chemical compound SC[C@H](N)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(C)C)C(O)=O HSAWNMMTZCLTPY-DCAQKATOSA-N 0.000 description 1
- IRKLTAKLAFUTLA-KATARQTJSA-N Cys-Thr-Lys Chemical compound C[C@@H](O)[C@H](NC(=O)[C@@H](N)CS)C(=O)N[C@@H](CCCCN)C(O)=O IRKLTAKLAFUTLA-KATARQTJSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- IGNGBUVODQLMRJ-CIUDSAMLSA-N Gln-Ala-Met Chemical compound [H]N[C@@H](CCC(N)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](CCSC)C(O)=O IGNGBUVODQLMRJ-CIUDSAMLSA-N 0.000 description 1
- LVSYIKGMLRHKME-IUCAKERBSA-N Gln-Gly-His Chemical compound C1=C(NC=N1)C[C@@H](C(=O)O)NC(=O)CNC(=O)[C@H](CCC(=O)N)N LVSYIKGMLRHKME-IUCAKERBSA-N 0.000 description 1
- ITYRYNUZHPNCIK-GUBZILKMSA-N Glu-Ala-Leu Chemical compound [H]N[C@@H](CCC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](CC(C)C)C(O)=O ITYRYNUZHPNCIK-GUBZILKMSA-N 0.000 description 1
- RSUVOPBMWMTVDI-XEGUGMAKSA-N Glu-Ala-Trp Chemical compound C1=CC=C2C(C[C@H](NC(=O)[C@@H](NC(=O)[C@@H](N)CCC(O)=O)C)C(O)=O)=CNC2=C1 RSUVOPBMWMTVDI-XEGUGMAKSA-N 0.000 description 1
- NLKVNZUFDPWPNL-YUMQZZPRSA-N Glu-Arg-Gly Chemical compound [H]N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)NCC(O)=O NLKVNZUFDPWPNL-YUMQZZPRSA-N 0.000 description 1
- WVTIBGWZUMJBFY-GUBZILKMSA-N Glu-His-Ser Chemical compound [H]N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC1=CNC=N1)C(=O)N[C@@H](CO)C(O)=O WVTIBGWZUMJBFY-GUBZILKMSA-N 0.000 description 1
- GMVCSRBOSIUTFC-FXQIFTODSA-N Glu-Ser-Glu Chemical compound [H]N[C@@H](CCC(O)=O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(O)=O)C(O)=O GMVCSRBOSIUTFC-FXQIFTODSA-N 0.000 description 1
- DLISPGXMKZTWQG-IFFSRLJSSA-N Glu-Thr-Val Chemical compound [H]N[C@@H](CCC(O)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](C(C)C)C(O)=O DLISPGXMKZTWQG-IFFSRLJSSA-N 0.000 description 1
- JDAYMLXPUJRSDJ-XIRDDKMYSA-N Glu-Trp-Arg Chemical compound C1=CC=C2C(C[C@H](NC(=O)[C@H](CCC(O)=O)N)C(=O)N[C@@H](CCCN=C(N)N)C(O)=O)=CNC2=C1 JDAYMLXPUJRSDJ-XIRDDKMYSA-N 0.000 description 1
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
- UGVQELHRNUDMAA-BYPYZUCNSA-N Gly-Ala-Gly Chemical compound [NH3+]CC(=O)N[C@@H](C)C(=O)NCC([O-])=O UGVQELHRNUDMAA-BYPYZUCNSA-N 0.000 description 1
- UXJHNZODTMHWRD-WHFBIAKZSA-N Gly-Asn-Ala Chemical compound [H]NCC(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](C)C(O)=O UXJHNZODTMHWRD-WHFBIAKZSA-N 0.000 description 1
- PAWIVEIWWYGBAM-YUMQZZPRSA-N Gly-Leu-Ala Chemical compound NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C)C(O)=O PAWIVEIWWYGBAM-YUMQZZPRSA-N 0.000 description 1
- GMTXWRIDLGTVFC-IUCAKERBSA-N Gly-Lys-Glu Chemical compound [H]NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCC(O)=O)C(O)=O GMTXWRIDLGTVFC-IUCAKERBSA-N 0.000 description 1
- MHXKHKWHPNETGG-QWRGUYRKSA-N Gly-Lys-Leu Chemical compound [H]NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(O)=O MHXKHKWHPNETGG-QWRGUYRKSA-N 0.000 description 1
- QAMMIGULQSIRCD-IRXDYDNUSA-N Gly-Phe-Tyr Chemical compound C([C@H](NC(=O)C[NH3+])C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C([O-])=O)C1=CC=CC=C1 QAMMIGULQSIRCD-IRXDYDNUSA-N 0.000 description 1
- FGPLUIQCSKGLTI-WDSKDSINSA-N Gly-Ser-Glu Chemical compound NCC(=O)N[C@@H](CO)C(=O)N[C@H](C(O)=O)CCC(O)=O FGPLUIQCSKGLTI-WDSKDSINSA-N 0.000 description 1
- ZLCLYFGMKFCDCN-XPUUQOCRSA-N Gly-Ser-Val Chemical compound CC(C)[C@H](NC(=O)[C@H](CO)NC(=O)CN)C(O)=O ZLCLYFGMKFCDCN-XPUUQOCRSA-N 0.000 description 1
- FZKFYOXDVWDELO-KBPBESRZSA-N His-Gly-Tyr Chemical compound [H]N[C@@H](CC1=CNC=N1)C(=O)NCC(=O)N[C@@H](CC1=CC=C(O)C=C1)C(O)=O FZKFYOXDVWDELO-KBPBESRZSA-N 0.000 description 1
- STGQSBKUYSPPIG-CIUDSAMLSA-N His-Ser-Asp Chemical compound OC(=O)C[C@@H](C(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](N)CC1=CN=CN1 STGQSBKUYSPPIG-CIUDSAMLSA-N 0.000 description 1
- 108090000604 Hydrolases Proteins 0.000 description 1
- FVEWRQXNISSYFO-ZPFDUUQYSA-N Ile-Arg-Glu Chemical compound CC[C@H](C)[C@@H](C(=O)N[C@@H](CCCN=C(N)N)C(=O)N[C@@H](CCC(=O)O)C(=O)O)N FVEWRQXNISSYFO-ZPFDUUQYSA-N 0.000 description 1
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 description 1
- LHSGPCFBGJHPCY-UHFFFAOYSA-N L-leucine-L-tyrosine Natural products CC(C)CC(N)C(=O)NC(C(O)=O)CC1=CC=C(O)C=C1 LHSGPCFBGJHPCY-UHFFFAOYSA-N 0.000 description 1
- GRZSCTXVCDUIPO-SRVKXCTJSA-N Leu-Arg-Gln Chemical compound [H]N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(N)=O)C(O)=O GRZSCTXVCDUIPO-SRVKXCTJSA-N 0.000 description 1
- ILJREDZFPHTUIE-GUBZILKMSA-N Leu-Asp-Glu Chemical compound [H]N[C@@H](CC(C)C)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(O)=O ILJREDZFPHTUIE-GUBZILKMSA-N 0.000 description 1
- ULXYQAJWJGLCNR-YUMQZZPRSA-N Leu-Asp-Gly Chemical compound CC(C)C[C@H](N)C(=O)N[C@@H](CC(O)=O)C(=O)NCC(O)=O ULXYQAJWJGLCNR-YUMQZZPRSA-N 0.000 description 1
- FIYMBBHGYNQFOP-IUCAKERBSA-N Leu-Gly-Gln Chemical compound CC(C)C[C@@H](C(=O)NCC(=O)N[C@@H](CCC(=O)N)C(=O)O)N FIYMBBHGYNQFOP-IUCAKERBSA-N 0.000 description 1
- HYIFFZAQXPUEAU-QWRGUYRKSA-N Leu-Gly-Leu Chemical compound CC(C)C[C@H](N)C(=O)NCC(=O)N[C@H](C(O)=O)CC(C)C HYIFFZAQXPUEAU-QWRGUYRKSA-N 0.000 description 1
- WXZOHBVPVKABQN-DCAQKATOSA-N Leu-Met-Asp Chemical compound CC(C)C[C@@H](C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(=O)O)C(=O)O)N WXZOHBVPVKABQN-DCAQKATOSA-N 0.000 description 1
- AIRUUHAOKGVJAD-JYJNAYRXSA-N Leu-Phe-Glu Chemical compound [H]N[C@@H](CC(C)C)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)N[C@@H](CCC(O)=O)C(O)=O AIRUUHAOKGVJAD-JYJNAYRXSA-N 0.000 description 1
- PTRKPHUGYULXPU-KKUMJFAQSA-N Leu-Phe-Ser Chemical compound [H]N[C@@H](CC(C)C)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)N[C@@H](CO)C(O)=O PTRKPHUGYULXPU-KKUMJFAQSA-N 0.000 description 1
- WMIOEVKKYIMVKI-DCAQKATOSA-N Leu-Pro-Ala Chemical compound [H]N[C@@H](CC(C)C)C(=O)N1CCC[C@H]1C(=O)N[C@@H](C)C(O)=O WMIOEVKKYIMVKI-DCAQKATOSA-N 0.000 description 1
- ADJWHHZETYAAAX-SRVKXCTJSA-N Leu-Ser-His Chemical compound CC(C)C[C@@H](C(=O)N[C@@H](CO)C(=O)N[C@@H](CC1=CN=CN1)C(=O)O)N ADJWHHZETYAAAX-SRVKXCTJSA-N 0.000 description 1
- PPGBXYKMUMHFBF-KATARQTJSA-N Leu-Ser-Thr Chemical compound [H]N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H]([C@@H](C)O)C(O)=O PPGBXYKMUMHFBF-KATARQTJSA-N 0.000 description 1
- ZDJQVSIPFLMNOX-RHYQMDGZSA-N Leu-Thr-Arg Chemical compound CC(C)C[C@H](N)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@H](C(O)=O)CCCN=C(N)N ZDJQVSIPFLMNOX-RHYQMDGZSA-N 0.000 description 1
- LCNASHSOFMRYFO-WDCWCFNPSA-N Leu-Thr-Gln Chemical compound CC(C)C[C@H](N)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@H](C(O)=O)CCC(N)=O LCNASHSOFMRYFO-WDCWCFNPSA-N 0.000 description 1
- ZJSZPXISKMDJKQ-JYJNAYRXSA-N Lys-Phe-Glu Chemical compound NCCCC[C@H](N)C(=O)N[C@H](C(=O)N[C@@H](CCC(O)=O)C(O)=O)CC1=CC=CC=C1 ZJSZPXISKMDJKQ-JYJNAYRXSA-N 0.000 description 1
- CTVJSFRHUOSCQQ-DCAQKATOSA-N Met-Arg-Glu Chemical compound CSCC[C@H](N)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(O)=O)C(O)=O CTVJSFRHUOSCQQ-DCAQKATOSA-N 0.000 description 1
- JYCQGAGDJQYEDB-GUBZILKMSA-N Met-Gln-Gln Chemical compound CSCC[C@H](N)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(N)=O)C(O)=O JYCQGAGDJQYEDB-GUBZILKMSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 108091007476 Microbial Esterases Proteins 0.000 description 1
- XMBSYZWANAQXEV-UHFFFAOYSA-N N-alpha-L-glutamyl-L-phenylalanine Natural products OC(=O)CCC(N)C(=O)NC(C(O)=O)CC1=CC=CC=C1 XMBSYZWANAQXEV-UHFFFAOYSA-N 0.000 description 1
- KZNQNBZMBZJQJO-UHFFFAOYSA-N N-glycyl-L-proline Natural products NCC(=O)N1CCCC1C(O)=O KZNQNBZMBZJQJO-UHFFFAOYSA-N 0.000 description 1
- 108010002311 N-glycylglutamic acid Proteins 0.000 description 1
- BQVUABVGYYSDCJ-UHFFFAOYSA-N Nalpha-L-Leucyl-L-tryptophan Natural products C1=CC=C2C(CC(NC(=O)C(N)CC(C)C)C(O)=O)=CNC2=C1 BQVUABVGYYSDCJ-UHFFFAOYSA-N 0.000 description 1
- NHCKESBLOMHIIE-IRXDYDNUSA-N Phe-Gly-Phe Chemical compound C([C@H](N)C(=O)NCC(=O)N[C@@H](CC=1C=CC=CC=1)C(O)=O)C1=CC=CC=C1 NHCKESBLOMHIIE-IRXDYDNUSA-N 0.000 description 1
- SWCOXQLDICUYOL-ULQDDVLXSA-N Phe-His-Arg Chemical compound [H]N[C@@H](CC1=CC=CC=C1)C(=O)N[C@@H](CC1=CNC=N1)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O SWCOXQLDICUYOL-ULQDDVLXSA-N 0.000 description 1
- SPXWRYVHOZVYBU-ULQDDVLXSA-N Phe-His-Val Chemical compound CC(C)[C@@H](C(=O)O)NC(=O)[C@H](CC1=CN=CN1)NC(=O)[C@H](CC2=CC=CC=C2)N SPXWRYVHOZVYBU-ULQDDVLXSA-N 0.000 description 1
- 229920001213 Polysorbate 20 Polymers 0.000 description 1
- DZZCICYRSZASNF-FXQIFTODSA-N Pro-Ala-Ala Chemical compound OC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@@H]1CCCN1 DZZCICYRSZASNF-FXQIFTODSA-N 0.000 description 1
- LHALYDBUDCWMDY-CIUDSAMLSA-N Pro-Glu-Ala Chemical compound C[C@H](NC(=O)[C@H](CCC(O)=O)NC(=O)[C@@H]1CCCN1)C(O)=O LHALYDBUDCWMDY-CIUDSAMLSA-N 0.000 description 1
- VPFGPKIWSDVTOY-SRVKXCTJSA-N Pro-Glu-His Chemical compound C1C[C@H](NC1)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CC2=CN=CN2)C(=O)O VPFGPKIWSDVTOY-SRVKXCTJSA-N 0.000 description 1
- WFHYFCWBLSKEMS-KKUMJFAQSA-N Pro-Glu-Phe Chemical compound N([C@@H](CCC(=O)O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(O)=O)C(=O)[C@@H]1CCCN1 WFHYFCWBLSKEMS-KKUMJFAQSA-N 0.000 description 1
- ULIWFCCJIOEHMU-BQBZGAKWSA-N Pro-Gly-Asp Chemical compound OC(=O)C[C@@H](C(O)=O)NC(=O)CNC(=O)[C@@H]1CCCN1 ULIWFCCJIOEHMU-BQBZGAKWSA-N 0.000 description 1
- FIDNSJUXESUDOV-JYJNAYRXSA-N Pro-Tyr-Val Chemical compound [H]N1CCC[C@H]1C(=O)N[C@@H](CC1=CC=C(O)C=C1)C(=O)N[C@@H](C(C)C)C(O)=O FIDNSJUXESUDOV-JYJNAYRXSA-N 0.000 description 1
- DOSZISJPMCYEHT-NAKRPEOUSA-N Ser-Ile-Val Chemical compound [H]N[C@@H](CO)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](C(C)C)C(O)=O DOSZISJPMCYEHT-NAKRPEOUSA-N 0.000 description 1
- VMLONWHIORGALA-SRVKXCTJSA-N Ser-Leu-Leu Chemical compound CC(C)C[C@@H](C([O-])=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H]([NH3+])CO VMLONWHIORGALA-SRVKXCTJSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- UTSWGQNAQRIHAI-UNQGMJICSA-N Thr-Arg-Phe Chemical compound NC(N)=NCCC[C@H](NC(=O)[C@@H](N)[C@H](O)C)C(=O)N[C@H](C(O)=O)CC1=CC=CC=C1 UTSWGQNAQRIHAI-UNQGMJICSA-N 0.000 description 1
- XOWKUMFHEZLKLT-CIQUZCHMSA-N Thr-Ile-Ala Chemical compound [H]N[C@@H]([C@@H](C)O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](C)C(O)=O XOWKUMFHEZLKLT-CIQUZCHMSA-N 0.000 description 1
- RFKVQLIXNVEOMB-WEDXCCLWSA-N Thr-Leu-Gly Chemical compound C[C@H]([C@@H](C(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)O)N)O RFKVQLIXNVEOMB-WEDXCCLWSA-N 0.000 description 1
- MXNAOGFNFNKUPD-JHYOHUSXSA-N Thr-Phe-Thr Chemical compound [H]N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)N[C@@H]([C@@H](C)O)C(O)=O MXNAOGFNFNKUPD-JHYOHUSXSA-N 0.000 description 1
- RVMNUBQWPVOUKH-HEIBUPTGSA-N Thr-Ser-Thr Chemical compound [H]N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CO)C(=O)N[C@@H]([C@@H](C)O)C(O)=O RVMNUBQWPVOUKH-HEIBUPTGSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- CXUFDWZBHKUGKK-CABZTGNLSA-N Trp-Ala-Gly Chemical compound C1=CC=C2C(C[C@H](N)C(=O)N[C@@H](C)C(=O)NCC(O)=O)=CNC2=C1 CXUFDWZBHKUGKK-CABZTGNLSA-N 0.000 description 1
- ZZDFLJFVSNQINX-HWHUXHBOSA-N Trp-Thr-Pro Chemical compound C[C@H]([C@@H](C(=O)N1CCC[C@@H]1C(=O)O)NC(=O)[C@H](CC2=CNC3=CC=CC=C32)N)O ZZDFLJFVSNQINX-HWHUXHBOSA-N 0.000 description 1
- FGJWNBBFAUHBEP-IHPCNDPISA-N Tyr-Asp-Trp Chemical compound C1=CC=C2C(=C1)C(=CN2)C[C@@H](C(=O)O)NC(=O)[C@H](CC(=O)O)NC(=O)[C@H](CC3=CC=C(C=C3)O)N FGJWNBBFAUHBEP-IHPCNDPISA-N 0.000 description 1
- NZFCWALTLNFHHC-JYJNAYRXSA-N Tyr-Glu-Leu Chemical compound CC(C)C[C@@H](C(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@@H](N)CC1=CC=C(O)C=C1 NZFCWALTLNFHHC-JYJNAYRXSA-N 0.000 description 1
- UEOOXDLMQZBPFR-ZKWXMUAHSA-N Val-Ala-Asn Chemical compound C[C@@H](C(=O)N[C@@H](CC(=O)N)C(=O)O)NC(=O)[C@H](C(C)C)N UEOOXDLMQZBPFR-ZKWXMUAHSA-N 0.000 description 1
- REJBPZVUHYNMEN-LSJOCFKGSA-N Val-Ala-His Chemical compound C[C@@H](C(=O)N[C@@H](CC1=CN=CN1)C(=O)O)NC(=O)[C@H](C(C)C)N REJBPZVUHYNMEN-LSJOCFKGSA-N 0.000 description 1
- ISERLACIZUGCDX-ZKWXMUAHSA-N Val-Asp-Ala Chemical compound C[C@@H](C(=O)O)NC(=O)[C@H](CC(=O)O)NC(=O)[C@H](C(C)C)N ISERLACIZUGCDX-ZKWXMUAHSA-N 0.000 description 1
- TZVUSFMQWPWHON-NHCYSSNCSA-N Val-Asp-Leu Chemical compound CC(C)C[C@@H](C(=O)O)NC(=O)[C@H](CC(=O)O)NC(=O)[C@H](C(C)C)N TZVUSFMQWPWHON-NHCYSSNCSA-N 0.000 description 1
- CPTQYHDSVGVGDZ-UKJIMTQDSA-N Val-Gln-Ile Chemical compound CC[C@H](C)[C@@H](C(=O)O)NC(=O)[C@H](CCC(=O)N)NC(=O)[C@H](C(C)C)N CPTQYHDSVGVGDZ-UKJIMTQDSA-N 0.000 description 1
- WFENBJPLZMPVAX-XVKPBYJWSA-N Val-Gly-Glu Chemical compound CC(C)[C@H](N)C(=O)NCC(=O)N[C@H](C(O)=O)CCC(O)=O WFENBJPLZMPVAX-XVKPBYJWSA-N 0.000 description 1
- PIFJAFRUVWZRKR-QMMMGPOBSA-N Val-Gly-Gly Chemical compound CC(C)[C@H]([NH3+])C(=O)NCC(=O)NCC([O-])=O PIFJAFRUVWZRKR-QMMMGPOBSA-N 0.000 description 1
- PQSNETRGCRUOGP-KKHAAJSZSA-N Val-Thr-Asn Chemical compound CC(C)[C@H](N)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@H](C(O)=O)CC(N)=O PQSNETRGCRUOGP-KKHAAJSZSA-N 0.000 description 1
- 108010036951 achatin I Proteins 0.000 description 1
- 108010024078 alanyl-glycyl-serine Proteins 0.000 description 1
- 108010041407 alanylaspartic acid Proteins 0.000 description 1
- 108010047495 alanylglycine Proteins 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 108010068380 arginylarginine Proteins 0.000 description 1
- 235000003704 aspartic acid Nutrition 0.000 description 1
- 108010093581 aspartyl-proline Proteins 0.000 description 1
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
- 239000011942 biocatalyst Substances 0.000 description 1
- 230000036983 biotransformation Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000005515 coenzyme Substances 0.000 description 1
- 108091036078 conserved sequence Proteins 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 238000010931 ester hydrolysis Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000013604 expression vector Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- 108010033719 glycyl-histidyl-glycine Proteins 0.000 description 1
- 108010020688 glycylhistidine Proteins 0.000 description 1
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 229940101629 l- methyl lactate Drugs 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 108010034529 leucyl-lysine Proteins 0.000 description 1
- 108010012058 leucyltyrosine Proteins 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- LPEKGGXMPWTOCB-VKHMYHEASA-N methyl (S)-lactate Chemical compound COC(=O)[C@H](C)O LPEKGGXMPWTOCB-VKHMYHEASA-N 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 108010070643 prolylglutamic acid Proteins 0.000 description 1
- 108010029020 prolylglycine Proteins 0.000 description 1
- 239000011535 reaction buffer Substances 0.000 description 1
- 238000003259 recombinant expression Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical group OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 108010029384 tryptophyl-histidine Proteins 0.000 description 1
- 108010045269 tryptophyltryptophan Proteins 0.000 description 1
- 108010005834 tyrosyl-alanyl-glycine Proteins 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- -1 washing Substances 0.000 description 1
- 238000004065 wastewater treatment Methods 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P41/00—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture
- C12P41/003—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by ester formation, lactone formation or the inverse reactions
- C12P41/004—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by ester formation, lactone formation or the inverse reactions by esterification of alcohol- or thiol groups in the enantiomers or the inverse reaction
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/02—Preparation of oxygen-containing organic compounds containing a hydroxy group
- C12P7/04—Preparation of oxygen-containing organic compounds containing a hydroxy group acyclic
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Biotechnology (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Analytical Chemistry (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
本发明公开了一种酯酶EstP00714在催化拆分外消旋乙酸芳樟酯得到(S)‑芳樟醇中的应用。本发明利用酯酶EstP00714作为催化剂，通过优化反应体系和反应条件，得到了对映体过量值96％以上的(S)‑芳樟醇，转化率达到55％。本发明与传统的化学拆分相比具有反应条件温和、无污染、对映体过量值高的优点。可用于生物医药、化妆品和精细化工等领域，具有非常大的应用价值。
Description
技术领域：
本发明属于生物化工和生物技术领域，具体涉及酯酶EstP00714在催化拆分外消旋乙酸芳樟酯得到(S)-芳樟醇中的应用。
背景技术：
酯酶(EC 3.1.1.1)广泛存在于动物、植物及微生物中，是一类催化水解或形成酯键的酶，作用的底物通常是脂肪链小于十个碳原子的酯类。酯酶属于α/β折叠水解酶超家族，催化中心由丝氨酸、天冬氨酸/谷氨酸、和组氨酸组成，保守序列为丝氨酸附近的五肽(GXSXG)序列。酯酶能催化水解、酯化、转酯化等多种化学反应，是一种很重要的工业生物催化剂，被广泛运用于精细化工、洗涤、医药、食品、造纸、皮革加工、纺织、废水处理和饲料工业等领域。从催化特性来看，酯酶具有高度的化学选择性和立体异构选择性，且反应不需要辅酶、反应条件温和、副产物少。在生产应用中的酯酶的另一显著特点是它能在异相系统(即油-水界面)或有机相中作用。在水相中，酯酶通常催化水解反应，而在有机相中，它却能催化酯化和转酯化反应。通过微生物酯酶的生物转化制备新型药物中间体或者去除药物消旋体的非有效成分，是一种重要的手性技术，有着非常广阔的应用前景，它可以为合成手性药物提供新的平台，为大量制备光学纯化合物提供新的方法。酶法选择性拆分消旋体化合物，具有立体专一性高，副反应少，产率高，产物光学纯度好以及反应条件温和的优点，所以是一种被广泛认可的拆分方法。
发明内容：
本发明的目的是提供一种酯酶EstP00714在催化拆分外消旋乙酸芳樟酯得到(S)-芳樟醇中的应用。
本发明从一株假单胞菌Pseudonocardia antitumoralis HUP007中开发得到一种酯酶EstP00714(其氨基酸序列如SEQ ID NO.2所示)及其编码基因EstP00714(其核苷酸序列如SEQ ID NO.1所示)，构建了含有酯酶基因EstP00714的重组表达载体和基因工程菌，培养基因工程菌后获得酯酶EstP00714，其可应用于催化酯类水解反应。
本发明的酯酶EstP00714在催化拆分外消旋乙酸芳樟酯得到(S)-芳樟醇中的应用，所述的酯酶EstP00714，其氨基酸序列如SEQ ID NO.2所示。
优选，所述的催化拆分外消旋乙酸芳樟酯得到(S)-芳樟醇是在有机溶剂和/或表面活性剂存在环境下进行的。
所述的有机溶剂优选为乙醇。
所述的表面活性剂优选为三聚磷酸钠。
所述的催化拆分外消旋乙酸芳樟酯得到(S)-芳樟醇的反应体系优选为：包含20mg/mL酯酶EstP00714、50mM底物外消旋乙酸芳樟酯、体积分数10％的乙醇和5g/L三聚磷酸钠，其余为pH6PBS缓冲液。
所述的催化拆分外消旋乙酸芳樟酯得到(S)-芳樟醇的反应温度为30℃，反应时间为2h。
本发明的酯酶基因Estp00714来自深假单胞菌Pseudonocardia antitumoralisHUP007(保存在中国科学院南海海洋研究所)。本发明的酯酶EstP00714，其氨基酸序列如SEQ ID NO.2所示，其编码基因Estp00714核苷酸序列如SEQ ID NO.1所示，该酯酶EstP00714公开于专利申请号：201610605466.3，发明名称：一种酯酶EstP00714及其编码基因和应用的专利申请中，酯酶EstP00714的制备方法见于该专利中，由此能够获得酯酶EstP00714酶粉(即纯化的酯酶EstP00714)。
本发明利用酯酶EstP00714作为催化剂，通过优化反应体系和反应条件，得到了对映体过量值96％以上的(S)-芳樟醇，转化率达到55％。本发明与传统的化学拆分相比具有反应条件温和、无污染、对映体过量值高的优点。可用于生物医药、化妆品和精细化工等领域，具有非常大的应用价值。
附图说明：
图1是底物浓度对酯酶EstP00714拆分外消旋乙酸芳樟酯的影响。
图2是酶浓度对酯酶EstP00714拆分外消旋乙酸芳樟酯的影响。
图3是反应时间对酯酶EstP00714拆分外消旋乙酸芳樟酯的影响。
图4是反应前外消旋乙酸芳樟酯气相色谱图；其中，1代表外消旋乙酸芳樟酯。
图5是(±)-芳樟醇气相色谱图；其中，R代表(R)-芳樟醇，S代表(S)-芳樟醇。
图6是反应后外消旋乙酸芳樟酯及产物芳樟醇气相色谱图；其中，R代表(R)-芳樟醇，S代表(S)-芳樟醇，1代表乙酸芳樟酯。
具体实施方式：
以下实施例是对本发明的进一步说明，而不是对本发明的限制。
本发明的酯酶基因Estp00714来自深假单胞菌Pseudonocardia antitumoralisHUP007，该菌保存在中国科学院南海海洋研究所实验室。本发明的酯酶EstP00714，其氨基酸序列如SEQ ID NO.2所示，其编码基因Estp00714核苷酸序列如SEQ ID NO.1所示，该酯酶EstP00714公开于专利申请号：201610605466.3，发明名称：一种酯酶EstP00714及其编码基因和应用的专利申请中，酯酶EstP00714的制备方法见于该专利中，由此能够获得纯化的酯酶EstP00714(即酯酶EstP00714酶粉)。
实施例1：酯酶EstP00714拆分外消旋乙酸芳樟酯
1.1反应pH和温度对酯酶EstP00714拆分外消旋乙酸芳樟酯的影响
不同pH反应体系为0.5mL，包含10mg酯酶EstP00714酶粉，50mM底物外消旋乙酸芳樟酯，其余为不同pH的反应缓冲液；在不同温度下反应2h。GC测定酯酶EstP00714拆分外消旋乙酸芳樟酯的立体选择性，根据峰面积计算产物对映体过量值(e.e.)和转化率(C)，结果见表1。
公式1：
公式2：
式中：AS和AR分别表示(S)-芳樟醇和(R)-芳樟醇的峰面积，A0和A表示反应前后乙酸芳樟酯的峰面积。
在pH6.0-10.0之间转化率(C)随pH的增大而增大，但e.e.随pH的增大而逐渐减小。在pH6.0时得到最高的e.e.92％。因此，酯酶EstP00714拆分外消旋乙酸芳樟酯的最适pH为6.0。
C随着温度升高先增加后减少，在25-35℃之间，e.e.降低不明显。当温度高于35℃时C显著降低，这与高温影响酶的活性有关。在30℃时取得最大转化率55％，e.e.达到94％。因此，酯酶EstP00714拆分外消旋乙酸芳樟酯的最适温度为30℃。
表1反应pH与温度对酯酶EstP00714拆分外消旋乙酸芳樟酯的影响
a表示PBS缓冲液，b表示Tris/HCl缓冲液
1.2有机溶剂对酯酶EstP00714拆分外消旋乙酸芳樟酯的影响
反应体系为0.5mL，包含10mg酯酶EstP00714酶粉，50mM底物外消旋乙酸芳樟酯，体积分数10％、30％的有机溶剂，其余为pH6.0PBS缓冲液；以未加有机溶剂为对照；在30℃下反应2h，用气相色谱手性柱检测，结果见表2。
表2有机溶剂对酯酶EstP00714拆分外消旋乙酸芳樟酯的影响
从表2中可看出大部分有机溶剂存在的情况下酯酶EstP00714的立体选择性都略有提高，但烷类不同程度的降低转化率。虽然在体积分数10％的异辛烷、正己烷和甲苯存在的情况下，e.e.达到98％，但其C相对降低比较明显。在体积分数10％的乙醇中，e.e.和C都有提高，分别达97％和52％。因此在后续实验中采用乙醇为助溶剂。
1.3表面活性剂对酯酶EstP00714拆分外消旋乙酸芳樟酯的影响
在优化条件下(30℃，pH6.0PBS缓冲液)，反应体系为0.5mL，包含10mg酯酶EstP00714酶粉，50mM底物外消旋乙酸芳樟酯，终浓度为体积分数10％的乙醇，1g/L、5g/L、10g/L的表面活性剂(三聚磷酸钠、Tween-20、Tween-80、TritonX-100)，其余为pH6.0PBS缓冲液；以未加表面活性剂为对照，在30℃下反应2h后，样品用于GC检测，结果见表3。从表3中可看出，与对照相比，4种表面活性剂对酯酶EstP00714拆分外消旋乙酸芳樟酯的e.e.无明显影响，5g/L三聚磷酸钠可以提高转化率到54％，因此在后续实验中加入5g/L的三聚磷酸钠。
表3表面活性剂对酯酶EstP00714拆分外消旋乙酸芳樟酯的影响
1.4底物浓度对酯酶EstP00714拆分外消旋乙酸芳樟酯的影响
在优化条件下(30℃，pH6.0PBS缓冲液)，反应体系为0.5mL，包含10mg酯酶EstP00714酶粉，10-100mM底物外消旋乙酸芳樟酯，体积分数10％的乙醇，5g/L三聚磷酸钠，其余为pH6.0PBS缓冲液；在30℃下反应2h后，样品用于GC检测，结果见图1。从图1中可看出，随着底物浓度增加，e.e.缓慢增加，转化率C逐渐下降。说明较高浓度的底物会抑制酶的反应，使转化率下降。底物浓度>50mM时，e.e.基本不变，因此，酯酶EstP00714拆分外消旋乙酸芳樟酯的最适底物浓度为50mM，e.e.和C分别为96％和50％。
1.5酶浓度对酯酶EstP00714拆分外消旋乙酸芳樟酯的影响
在优化条件下(30℃，pH6.0PBS缓冲液)，反应体系为0.5mL，包含5-35mg酯酶EstP00714酶粉，50mM底物外消旋乙酸芳樟酯，体积分数10％的乙醇，5g/L三聚磷酸钠，其余为pH6.0PBS缓冲液；在30℃下反应2h后GC检测，结果见图2。从图2中可以看出，随酶浓度的增加，e.e.和转化率变化不是很大。酶浓度为20mg/mL时，e.e.和转化率分别为96％和53％。
1.6反应时间对酯酶EstP00714拆分外消旋乙酸芳樟酯的影响
在优化条件下(30℃，pH6.0PBS缓冲液)，反应体系为0.5mL，包含10mg酯酶EstP00714酶粉，50mM底物外消旋乙酸芳樟酯，体积分数10％的乙醇，5g/L三聚磷酸钠，其余为pH6.0PBS缓冲液；在30℃下反应，每间隔1h取出500μL，用乙酸乙酯萃取，无水硫酸钠除水，加入L-乳酸甲酯作为内标，用气相色谱手性柱检测。不同反应时间酯酶EstP00714拆分外消旋乙酸芳樟酯的结果见图3。
从图3中可看出，随着时间的延长，C逐渐升高，经过2h反应，e.e.和转化率基本达到最高，分别达到96％和55％。2h之后，转化率和e.e.变化都不明显。图4、5、6分别是反应前外消旋乙酸芳樟酯、(±)-芳樟醇气相色谱图及反应后乙酸芳樟酯和芳樟醇气相色谱图。
序列表
<110> 中国科学院南海海洋研究所
<120> 酯酶EstP00714在催化拆分外消旋乙酸芳樟酯得到(S)-芳樟醇中的应用
<160> 2
<170> SIPOSequenceListing 1.0
<210> 1
<211> 1146
<212> DNA
<213> 假单胞菌HUP007 (Pseudonocardia antitumoralis HUP007)
<400> 1
gtgcagatcc agggtcacta tgagctgaag ttcgaggcgg tgcgcgatgc cttcgccgcg 60
ttgttcgagg atccccagga acgtggtgcc gcattgtgca tccaggttgg cggcgagacc 120
gtggtcgacc tgtgggccgg cagcgccgac aaggacggcc gcgaggcctg gcacagcgat 180
accatcgcca acctgttctc ctgcaccaag accttcaccg ccgtcaccgc cctgcaactg 240
gtgggcgagg gcaagctggc cctcgatgcg ccggtggcgc gctactggcc ggagttcgcc 300
caggccggca aggagcaggt caccctgcgc cagttgctca gccaccgcgc cggcctgccg 360
gccatccgcg agctgctgcc ggccgaggcg ctgtacgact ggcaagccat ggttgatgcc 420
ctggccgccg aagcgccctg gtggacaccc ggaagcgaac acggttacgc ggcgatcacc 480
tatggctggc tgatcggtga gctgatccgc cgcgccgacg gtcgcggccc gggcgactcg 540
atcgtggctc gcaccgcccg gccattgggg ttggatttcc atgtcggcct ggccgacgac 600
gagttccacc gcgtggcgca tatcgcccgc ggcaagggca accccggcga tgccgcggcc 660
cagcgcctgc tgcaggtcac catgcgcgag cccgaggccc tgtcgacccg ggccttcacc 720
aacccgccgg cgatcctcac cagcaccaac aagcccgaat ggcggcgcat gcagcagcca 780
gcggccaatg gccacggcaa cgcccgcagc ctggcgggct tctatgccgg cctgctcgac 840
ggcagcctgc tggagtccga gctgctcgac gaactgaccc gcgagcacag cctcggccag 900
gaccgcaccc tgttgaccca gacccgcttc ggcctgggct gcatgctcga ccagccagaa 960
gtggccaacg ccactttcgg ccttggcgcg cgggcgttcg gccatcccgg cgcgggcggc 1020
tcggtcggct ttgccgaccc cgaacacgac gtggcctttg gcttcgtcac caataccctg 1080
ggcccctatg tgctgatgga cccgcgcgct caacgcctgg tgcgtgtcct tggcagttgc 1140
ctttga 1146
<210> 2
<211> 381
<212> PRT
<213> 假单胞菌HUP007 (Pseudonocardia antitumoralis HUP007)
<400> 2
Val Gln Ile Gln Gly His Tyr Glu Leu Lys Phe Glu Ala Val Arg Asp
1 5 10 15
Ala Phe Ala Ala Leu Phe Glu Asp Pro Gln Glu Arg Gly Ala Ala Leu
20 25 30
Cys Ile Gln Val Gly Gly Glu Thr Val Val Asp Leu Trp Ala Gly Ser
35 40 45
Ala Asp Lys Asp Gly Arg Glu Ala Trp His Ser Asp Thr Ile Ala Asn
50 55 60
Leu Phe Ser Cys Thr Lys Thr Phe Thr Ala Val Thr Ala Leu Gln Leu
65 70 75 80
Val Gly Glu Gly Lys Leu Ala Leu Asp Ala Pro Val Ala Arg Tyr Trp
85 90 95
Pro Glu Phe Ala Gln Ala Gly Lys Glu Gln Val Thr Leu Arg Gln Leu
100 105 110
Leu Ser His Arg Ala Gly Leu Pro Ala Ile Arg Glu Leu Leu Pro Ala
115 120 125
Glu Ala Leu Tyr Asp Trp Gln Ala Met Val Asp Ala Leu Ala Ala Glu
130 135 140
Ala Pro Trp Trp Thr Pro Gly Ser Glu His Gly Tyr Ala Ala Ile Thr
145 150 155 160
Tyr Gly Trp Leu Ile Gly Glu Leu Ile Arg Arg Ala Asp Gly Arg Gly
165 170 175
Pro Gly Asp Ser Ile Val Ala Arg Thr Ala Arg Pro Leu Gly Leu Asp
180 185 190
Phe His Val Gly Leu Ala Asp Asp Glu Phe His Arg Val Ala His Ile
195 200 205
Ala Arg Gly Lys Gly Asn Pro Gly Asp Ala Ala Ala Gln Arg Leu Leu
210 215 220
Gln Val Thr Met Arg Glu Pro Glu Ala Leu Ser Thr Arg Ala Phe Thr
225 230 235 240
Asn Pro Pro Ala Ile Leu Thr Ser Thr Asn Lys Pro Glu Trp Arg Arg
245 250 255
Met Gln Gln Pro Ala Ala Asn Gly His Gly Asn Ala Arg Ser Leu Ala
260 265 270
Gly Phe Tyr Ala Gly Leu Leu Asp Gly Ser Leu Leu Glu Ser Glu Leu
275 280 285
Leu Asp Glu Leu Thr Arg Glu His Ser Leu Gly Gln Asp Arg Thr Leu
290 295 300
Leu Thr Gln Thr Arg Phe Gly Leu Gly Cys Met Leu Asp Gln Pro Glu
305 310 315 320
Val Ala Asn Ala Thr Phe Gly Leu Gly Ala Arg Ala Phe Gly His Pro
325 330 335
Gly Ala Gly Gly Ser Val Gly Phe Ala Asp Pro Glu His Asp Val Ala
340 345 350
Phe Gly Phe Val Thr Asn Thr Leu Gly Pro Tyr Val Leu Met Asp Pro
355 360 365
Arg Ala Gln Arg Leu Val Arg Val Leu Gly Ser Cys Leu
370 375 380
Claims (6)
1.酯酶EstP00714在催化拆分外消旋乙酸芳樟酯得到(S)-芳樟醇中的应用，所述的酯酶EstP00714，其氨基酸序列如SEQ ID NO.2所示。
2.根据权利要求1所述的应用，其特征在于，所述的催化拆分外消旋乙酸芳樟酯得到(S)-芳樟醇是在有机溶剂和/或表面活性剂存在环境下进行的。
3.根据权利要求2所述的应用，其特征在于，所述的有机溶剂为乙醇。
4.根据权利要求2或3所述的应用，其特征在于，所述的表面活性剂为三聚磷酸钠。
5.根据权利要求4所述的应用，其特征在于，所述的催化拆分外消旋乙酸芳樟酯得到(S)-芳樟醇的反应体系为：包含20mg/mL酯酶EstP00714、50mM底物外消旋乙酸芳樟酯、体积分数10％的乙醇和5g/L三聚磷酸钠，其余为pH6的PBS缓冲液。
6.根据权利要求5所述的应用，其特征在于，所述的催化拆分外消旋乙酸芳樟酯得到(S)-芳樟醇的反应温度为30℃，反应时间为2h。
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810078725.0A CN108330154B (zh) | 2018-01-26 | 2018-01-26 | 酯酶EstP00714在催化拆分外消旋乙酸芳樟酯得到(S)-芳樟醇中的应用 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810078725.0A CN108330154B (zh) | 2018-01-26 | 2018-01-26 | 酯酶EstP00714在催化拆分外消旋乙酸芳樟酯得到(S)-芳樟醇中的应用 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN108330154A CN108330154A (zh) | 2018-07-27 |
| CN108330154B true CN108330154B (zh) | 2020-08-18 |
Family
ID=62925939
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201810078725.0A Expired - Fee Related CN108330154B (zh) | 2018-01-26 | 2018-01-26 | 酯酶EstP00714在催化拆分外消旋乙酸芳樟酯得到(S)-芳樟醇中的应用 |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN108330154B (zh) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN117070494B (zh) * | 2023-10-13 | 2024-01-19 | 天津凯莱英生物科技有限公司 | 酯酶突变体及其应用 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003031609A1 (de) * | 2001-10-09 | 2003-04-17 | Degussa Ag | Esterase esta aus rhodococcus sp. |
| CN106119224A (zh) * | 2016-07-27 | 2016-11-16 | 中国科学院南海海洋研究所 | 一种酯酶EstP00714及其编码基因和应用 |
-
2018
- 2018-01-26 CN CN201810078725.0A patent/CN108330154B/zh not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003031609A1 (de) * | 2001-10-09 | 2003-04-17 | Degussa Ag | Esterase esta aus rhodococcus sp. |
| CN106119224A (zh) * | 2016-07-27 | 2016-11-16 | 中国科学院南海海洋研究所 | 一种酯酶EstP00714及其编码基因和应用 |
Non-Patent Citations (1)
| Title |
|---|
| 一个新颖南极微生物酯酶EST112-2的功能鉴定和在手性叔醇(S)-芳樟醇制备中的应用（英文）;邓盾等;《有机化学》;20180118;第38卷(第5期);第1187-1192页 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN108330154A (zh) | 2018-07-27 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Palomo et al. | Synthesis of enantiomerically pure glycidol via a fully enantioselective lipase-catalyzed resolution | |
| CN104962533B (zh) | 一种新型酯酶及其编码基因和在拆分(±)-1-苯乙醇和(±)-乙酸苏合香酯中的应用 | |
| Machado et al. | Kinetic resolution of (R, S)-1, 2-isopropylidene glycerol (solketal) ester derivatives by lipases | |
| Oh et al. | Characterization of a novel esterase isolated from intertidal flat metagenome and its tertiary alcohols synthesis | |
| CN104745547A (zh) | 一种环氧化物水解酶突变体、工程菌及其应用 | |
| Kotik et al. | Cloning of an epoxide hydrolase-encoding gene from Aspergillus niger M200, overexpression in E. coli, and modification of activity and enantioselectivity of the enzyme by protein engineering | |
| CN105543190B (zh) | 一种酯酶bse00077及其编码基因和应用 | |
| WO1998053081A1 (en) | Enantioselective epoxide hydrolases and genes encoding these | |
| CN108285895B (zh) | 一种酯酶EstC11及其编码基因和应用 | |
| CN106754818B (zh) | 一种耐热酯酶突变体及其制备方法和应用 | |
| CN108330154B (zh) | 酯酶EstP00714在催化拆分外消旋乙酸芳樟酯得到(S)-芳樟醇中的应用 | |
| Kim et al. | Construction of an engineered biocatalyst system for the production of medium‐chain α, ω‐dicarboxylic acids from medium‐chain ω‐hydroxycarboxylic acids | |
| Dröge et al. | Paralogous gene analysis reveals a highly enantioselective 1, 2‐O‐isopropylideneglycerol caprylate esterase of Bacillus subtilis | |
| CN107586793B (zh) | 制备具有多个手性中心的醇化合物的方法 | |
| CN103131659B (zh) | 一种耐有机溶剂脂肪酶、其编码基因、产生菌株及应用 | |
| Su et al. | Functional expression of Serratia marcescens H30 lipase in Escherichia coli for efficient kinetic resolution of racemic alcohols in organic solvents | |
| Lehmann et al. | Characterization of a novel Pseudomonas stutzeri lipase/esterase with potential application in the production of chiral secondary alcohols | |
| CN110257352B (zh) | 一种环氧化物水解酶及其用途 | |
| JP3507860B2 (ja) | 酵母由来の新規リパーゼｃｓ２ | |
| CN104480084B (zh) | 一种耐多种纯有机溶剂的脂肪酶及其编码基因和在多种高产酯类化合物合成中的应用 | |
| US5457051A (en) | Enantioselective hydrolysis of ketoprofen esters by beauveria bassiana and enzymes derived therefrom | |
| EP4397754A1 (en) | Enzymatic agent for transesterification containing lipase as active ingredient | |
| Musidlowska-Persson et al. | Site directed mutagenesis of recombinant pig liver esterase yields mutants with altered enantioselectivity | |
| CN106119224B (zh) | 一种酯酶EstP00714及其编码基因和应用 | |
| EP0529085A1 (en) | Process for producing optically active 3-chloro-1-phenyl-1-propanol and derivative thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| CB02 | Change of applicant information | ||
| CB02 | Change of applicant information |
Address after: No.1119 Haibin Road, Nansha District, Guangzhou City, Guangdong Province Applicant after: SOUTH CHINA SEA INSTITUTE OF OCEANOLOGY, CHINESE ACADEMY OF SCIENCES Address before: 510301 No. 164 West Xingang Road, Guangdong, Guangzhou Applicant before: SOUTH CHINA SEA INSTITUTE OF OCEANOLOGY, CHINESE ACADEMY OF SCIENCES |
|
| GR01 | Patent grant | ||
| GR01 | Patent grant | ||
| CF01 | Termination of patent right due to non-payment of annual fee | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20200818 |