CN109589946A - 一种羧基功能化多孔环糊精聚合物及其在吸附和分离溶菌酶中的应用 - Google Patents
一种羧基功能化多孔环糊精聚合物及其在吸附和分离溶菌酶中的应用 Download PDFInfo
- Publication number
- CN109589946A CN109589946A CN201811627996.3A CN201811627996A CN109589946A CN 109589946 A CN109589946 A CN 109589946A CN 201811627996 A CN201811627996 A CN 201811627996A CN 109589946 A CN109589946 A CN 109589946A
- Authority
- CN
- China
- Prior art keywords
- lysozyme
- carboxyl
- functional
- porous cyclodextrin
- porous
- 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.)
- Granted
Links
- 229920000858 Cyclodextrin Polymers 0.000 title claims abstract description 40
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 title claims abstract description 37
- 102000016943 Muramidase Human genes 0.000 title claims abstract description 36
- 108010014251 Muramidase Proteins 0.000 title claims abstract description 36
- 108010062010 N-Acetylmuramoyl-L-alanine Amidase Proteins 0.000 title claims abstract description 36
- 229960000274 lysozyme Drugs 0.000 title claims abstract description 36
- 235000010335 lysozyme Nutrition 0.000 title claims abstract description 36
- 239000004325 lysozyme Substances 0.000 title claims abstract description 36
- 239000002861 polymer material Substances 0.000 claims abstract description 20
- 239000000463 material Substances 0.000 claims abstract description 14
- QCVGEOXPDFCNHA-UHFFFAOYSA-N 5,5-dimethyl-2,4-dioxo-1,3-oxazolidine-3-carboxamide Chemical compound CC1(C)OC(=O)N(C(N)=O)C1=O QCVGEOXPDFCNHA-UHFFFAOYSA-N 0.000 claims abstract description 13
- 108010000912 Egg Proteins Proteins 0.000 claims abstract description 13
- 102000002322 Egg Proteins Human genes 0.000 claims abstract description 13
- 235000014103 egg white Nutrition 0.000 claims abstract description 13
- 210000000969 egg white Anatomy 0.000 claims abstract description 13
- 238000000926 separation method Methods 0.000 claims abstract description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 8
- PCRSJGWFEMHHEW-UHFFFAOYSA-N 2,3,5,6-tetrafluorobenzene-1,4-dicarbonitrile Chemical compound FC1=C(F)C(C#N)=C(F)C(F)=C1C#N PCRSJGWFEMHHEW-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000003463 adsorbent Substances 0.000 claims abstract description 5
- 125000000524 functional group Chemical group 0.000 claims abstract description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 3
- 230000007062 hydrolysis Effects 0.000 claims abstract description 3
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 3
- 238000010521 absorption reaction Methods 0.000 claims description 10
- 239000003513 alkali Substances 0.000 claims description 2
- 239000002585 base Substances 0.000 claims description 2
- 238000001179 sorption measurement Methods 0.000 abstract description 12
- 229920000642 polymer Polymers 0.000 abstract description 6
- 230000009881 electrostatic interaction Effects 0.000 abstract 1
- 230000001681 protective effect Effects 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 239000000243 solution Substances 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 5
- 239000002048 multi walled nanotube Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 235000013601 eggs Nutrition 0.000 description 4
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000006228 supernatant Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- 238000010828 elution Methods 0.000 description 3
- 239000002122 magnetic nanoparticle Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 229920001448 anionic polyelectrolyte Polymers 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000009514 concussion Effects 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229940088598 enzyme Drugs 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000004005 microsphere Substances 0.000 description 2
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- LRWZZZWJMFNZIK-UHFFFAOYSA-N 2-chloro-3-methyloxirane Chemical compound CC1OC1Cl LRWZZZWJMFNZIK-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- SRUWWOSWHXIIIA-UKPGNTDSSA-N Cyanoginosin Chemical compound N1C(=O)[C@H](CCCN=C(N)N)NC(=O)[C@@H](C)[C@H](C(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](C)NC(=O)C(=C)N(C)C(=O)CC[C@H](C(O)=O)N(C)C(=O)[C@@H](C)[C@@H]1\C=C\C(\C)=C\[C@H](C)[C@@H](O)CC1=CC=CC=C1 SRUWWOSWHXIIIA-UKPGNTDSSA-N 0.000 description 1
- 239000001116 FEMA 4028 Substances 0.000 description 1
- 102000006395 Globulins Human genes 0.000 description 1
- 108010044091 Globulins Proteins 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 108010049746 Microcystins Proteins 0.000 description 1
- 108010058846 Ovalbumin Proteins 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000000274 adsorptive effect Effects 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000002421 anti-septic effect Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 230000000840 anti-viral effect Effects 0.000 description 1
- 229940064004 antiseptic throat preparations Drugs 0.000 description 1
- WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 description 1
- 235000011175 beta-cyclodextrine Nutrition 0.000 description 1
- 229960004853 betadex Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000013270 controlled release Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 238000007306 functionalization reaction Methods 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 239000002608 ionic liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 108010067094 microcystin Proteins 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229920000344 molecularly imprinted polymer Polymers 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229940092253 ovalbumin Drugs 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 238000002604 ultrasonography Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/22—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material
- B01J20/26—Synthetic macromolecular compounds
- B01J20/265—Synthetic macromolecular compounds modified or post-treated polymers
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F1/00—Treatment of water, waste water, or sewage
- C02F1/28—Treatment of water, waste water, or sewage by sorption
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F1/00—Treatment of water, waste water, or sewage
- C02F1/28—Treatment of water, waste water, or sewage by sorption
- C02F1/285—Treatment of water, waste water, or sewage by sorption using synthetic organic sorbents
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
- C12N9/14—Hydrolases (3)
- C12N9/24—Hydrolases (3) acting on glycosyl compounds (3.2)
- C12N9/2402—Hydrolases (3) acting on glycosyl compounds (3.2) hydrolysing O- and S- glycosyl compounds (3.2.1)
- C12N9/2462—Lysozyme (3.2.1.17)
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12Y—ENZYMES
- C12Y302/00—Hydrolases acting on glycosyl compounds, i.e. glycosylases (3.2)
- C12Y302/01—Glycosidases, i.e. enzymes hydrolysing O- and S-glycosyl compounds (3.2.1)
- C12Y302/01017—Lysozyme (3.2.1.17)
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- General Engineering & Computer Science (AREA)
- Water Supply & Treatment (AREA)
- General Health & Medical Sciences (AREA)
- Hydrology & Water Resources (AREA)
- Biochemistry (AREA)
- Environmental & Geological Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Analytical Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Biomedical Technology (AREA)
- Biotechnology (AREA)
- Microbiology (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
- Peptides Or Proteins (AREA)
Abstract
本发明公开了一种羧基功能化的多孔环糊精聚合物材料及其在吸附和分离溶菌酶中的应用。该材料是将四氟对苯二腈交联的多孔环糊精聚合物通过碱催化水解，使其表面的氰基转化为羧基，得到的表面富含羧基官能团的多孔环糊精聚合物材料。本发明借助于聚合物的多孔性，环糊精对溶菌酶的保护作用，以及聚合物表面羧基与溶菌酶的静电作用，将该材料作为一种新型吸附剂用于溶菌酶的吸附，最大吸附能力达到1520mg g‑1，且对溶菌酶有选择性，可用于分离鸡蛋清中的溶菌酶。
Description
技术领域
本发明属于分析化学、生物技术领域，具体涉及一种功能化材料及其在吸附和分离溶菌酶中的应用。
背景技术
溶菌酶是一种碱性球蛋白，广泛存在于人体的各种组织、哺乳动物的分泌物和家禽的蛋清中，其中蛋清含量最多约为3.4％。溶菌酶在工业和医疗领域具有很高的应用价值，可作为天然食品防腐剂，具有抗菌、抗病毒、抗肿瘤作用。因此，研究选择性好、吸附性能好的材料对蛋清中溶菌酶的分离具有实际意义。
近年来，一些新的吸附剂被广泛应用于溶菌酶分离，如溶菌酶印迹的磁性二氧化硅微球(Chen,J.；Lei,S.；Xie,Y.；Wang,M.；Yang,J.；Ge,X.Fabrication of High-Performance Magnetic Lysozyme-Imprinted Microsphere and Its NIR-ResponsiveControlled Release Property.ACS Appl.Mater.Interfaces 2015,7,28606-28615.)、聚(4-苯乙烯磺酸钠)修饰的磁性纳米颗粒(Chen,J.；Lin,Y.；Jia,L.Preparation ofAnionic Polyelectrolyte Modified Magnetic Nanoparticles for Rapid andEfficient Separation of Lysozyme from Egg White.J.Chromatogr.A 2015,1388,43-51.)、磺酰基和羧基修饰的硬脂醇包裹的环氧氯丙烷材料(Anirudhan,T.S.；Aswathy,E.S.；Deepa,J.R.Adsorptive Separation of Lysozyme from Aqueous Solutions UsingSulphonyl and Carboxyl Functionalized Stearyl Alcohol Grafted Epichlorohydrin.J.Polym.Environ.2017,25,101-114.)、磁性离子液体分子印迹聚合物(Wang,S.S.；Yang,S.M.；Hsin,A.；Chang,Y.K.Dye-Affinity Nanofibrous Membrane for Adsorptionof Lysozyme:Preparation and Performance Evaluation.FoodTechnol.Biotechnol.2018,56,40-50.)、染料亲和性纳米纤维膜(Enayatpour,B.；Rajabi,M.；Moradi,O.；Asdolehzade,N.；Nayak,A.；Agarwal,S.；Gupta,V.K.Adsorption Kineticsof Lysozyme on Multi-Walled Carbon Nanotubes and Amino Functionalized Multi-Walled Carbon Nanotubes from Aqueous Solution.J.Mol.Liq.2018,254,93-97.)、功能化的多壁碳纳米管(Enayatpour,B.；Rajabi,M.；Moradi,O.；Asdolehzade,N.；Nayak,A.；Agarwal,S.；Gupta,V.K.Adsorption Kinetics of Lysozyme on Multi-Walled CarbonNanotubes and Amino Functionalized Multi-Walled Carbon Nanotubes from AqueousSolution.J.Mol.Liq.2018,254,93-97.)等。但，由于溶菌酶特殊的结构和较大的分子尺寸使这些吸附剂对其吸附能力受到限制。
四氟对苯二腈交联的多孔环糊精聚合物(Alsbaiee,A.；Smith,B.J.；Xiao,L.；Ling,Y.；Helbling,D.E.；Dichtel,W.R.Rapid Removal of Organic Micropollutantsfrom Water by a Porousβ-cyclodextrin Polymer.Nature 2016,529,190-194.；Ling,Y.；Klemes,M.J.；Xiao,L.；Alsbaiee,A.；Dichtel,W.R.；Helbling,D.E.BenchmarkingMicropollutant Removal by Activated Carbon and Porousβ-Cyclodextrin Polymersunder Environmentally Relevant Scenarios.Environ.Sci.Technol.2017,51,7590-7598.；Li,C.；Klemes,M.J.；Dichtel,W.R.；Helbling,D.E.Tetrafluoroterephthalonitrile-Crosslinked Beta-Cyclodextrin Polymers for Efficient Extraction andRecovery of Organic Micropollutants from Water.J.Chromatogr.A2018,1541,52-56.)相比传统活性炭具有吸附速率快，吸附能力高等优点，受到了越来越多人的关注。随后，Alsbaieek课题组将多孔环糊精聚合物修饰在棉纤维上，用于吸附水和空气中的有机污染物；Zhang等人将多孔环糊精聚合物修饰在磁性微球上，用于富集环境水样中的微囊藻毒素(Zhang,W.；Lin,M.；Wang,M.；Tong,P.；Lu,Q.；Zhang,L.Magnetic Porous Beta-cyclodextrinPolymer for Magnetic Solid-Phase Extractionof Microcystins fromEnvironmental Water Samples.J.Chromatogr.A2017,1503,1-11.)。但尚无通过官能团转换对多孔环糊精聚合物进行修饰的文献。
发明内容
本发明的目的是提供一种选择性好、吸附性能好的羧基功能化多孔环糊精聚合物材料，并为该材料提供新的应用。
针对上述目的，本发明所采用的羧基功能化多孔环糊精聚合物材料是将四氟对苯二腈交联的多孔环糊精聚合物通过碱催化水解，使其表面的氰基转化为羧基，得到的表面富含羧基官能团的多孔环糊精聚合物材料。
上述羧基功能化多孔环糊精聚合物材料的制备方法为：将四氟对苯二腈交联的多孔环糊精聚合物粉末和质量分数为20％～35％的NaOH溶液(以去离子水和乙醇体积比为1:1的混合液为溶剂配制而成)混合，在110～130℃下搅拌回流24～48小时。反应结束后，分离、洗涤、干燥，得到羧基功能化多孔环糊精聚合物材料。
本发明羧基功能化多孔环糊精聚合物材料作为吸附剂在选择性吸附溶液中溶菌酶的应用。使用本发明的羧基功能化多孔环糊精聚合物材料吸附水溶液中的溶菌酶，最大饱和吸附量为1520mg g-1，且在pH＝9.0的条件下，吸附效果最好。
本发明羧基功能化多孔环糊精聚合物材料在分离蛋清中溶菌酶的应用。在鸡蛋清溶液中，本发明的羧基功能化多孔环糊精聚合物材料能选择性地分离溶液中的溶菌酶。
本发明羧基功能化多孔环糊精聚合物材料结构中含有适量的内部空腔，丰富的羧基和环糊精单体，且在中性条件显电负性，以上优点可以选择性地吸附溶菌酶，该材料在溶菌酶吸附和分离的相关领域有潜在的应用价值。
附图说明
图1是本发明羧基功能化多孔环糊精聚合物材料合成示意图。
图2是本发明羧基功能化多孔环糊精聚合物材料对蛋清中溶菌酶的分离效果图。
具体实施方式
下面结合附图和实施例对本发明进一步详细说明，但本发明的保护范围不仅限于这些实施例。
实施例1
将0.2g四氟对苯二腈交联的多孔环糊精聚合物粉末和20mL质量分数为30％的NaOH溶液(以去离子水和乙醇体积比为1:1的混合液为溶剂配制而成)加入圆底烧瓶中，在120℃下搅拌回流48小时。反应结束后，通过离心过滤收集固体，将收集到的固体样品浸泡在水中(通过加入几滴盐酸将pH调节至4～5)，在酸性水中超声10min，离心过滤，然后重复用水洗涤至中性。最后通过冷冻干燥12h，得到浅褐色的固体，即羧基功能化多孔环糊精聚合物材料，其结构示意图如图1所示。
实施例2
实施例1制备的羧基功能化多孔环糊精聚合物材料在选择性吸附溶液中溶菌酶的应用，具体方法如下：
称取4mg羧基功能化多孔环糊精聚合物材料，加入5mL溶菌酶溶液(1.5mgmL-1，pH＝9.0)，在25℃恒温摇床上进行震荡吸附，结束后离心，取上清液在280nm波长下进行紫外检测。实验结果显示该材料对溶菌酶的最大饱和吸附量为1520mg g-1。
实施例3
实施例1制备的羧基功能化多孔环糊精聚合物材料在分离蛋清中溶菌酶的应用根据文献(Chen,J.；Lin,Y.；Jia,L.Preparation of Anionic Polyelectrolyte ModifiedMagnetic Nanoparticles for Rapid and Efficient Separation of Lysozyme fromEgg White.J.Chromatogr.A 2015,1388,43-51.)对鸡蛋进行相应的处理获得蛋清储备液。
称取30mg羧基功能化多孔环糊精聚合物材料，加入5mL鸡蛋清溶液，在25℃恒温摇床上进行震荡吸附，结束后离心，将上清液倒出，剩余吸附有溶菌酶的材料用1.0mol/LNaCl水溶液洗脱，最后对稀释的鸡蛋清溶液、吸附后的上清液及洗脱后的溶菌酶溶液在280nm波长下进行HPLC分析。测定结果如图2所示。
由图2可见，稀释的鸡蛋清溶液经过HPLC分析，三种主要的蛋白：卵白蛋白、伴清蛋白和溶菌酶可以很好的分离，在加入羧基功能化多孔环糊精聚合物材料吸附后，上清液中溶菌酶的含量很少，经洗脱液洗脱后，可以得到纯度较高的溶菌酶。
Claims (3)
1.一种羧基功能化多孔环糊精聚合物材料，其特征在于：该材料是将四氟对苯二腈交联的多孔环糊精聚合物通过碱催化水解，使其表面的氰基转化为羧基，得到的表面富含羧基官能团的多孔环糊精聚合物材料。
2.权利要求1所述的羧基功能化多孔环糊精聚合物材料作为吸附剂在选择性吸附溶液中溶菌酶的应用。
3.权利要求1所述的羧基功能化多孔环糊精聚合物材料在分离蛋清中溶菌酶的应用。
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811627996.3A CN109589946B (zh) | 2018-12-28 | 2018-12-28 | 一种羧基功能化多孔环糊精聚合物及其在吸附和分离溶菌酶中的应用 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811627996.3A CN109589946B (zh) | 2018-12-28 | 2018-12-28 | 一种羧基功能化多孔环糊精聚合物及其在吸附和分离溶菌酶中的应用 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN109589946A true CN109589946A (zh) | 2019-04-09 |
| CN109589946B CN109589946B (zh) | 2021-03-30 |
Family
ID=65964836
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201811627996.3A Expired - Fee Related CN109589946B (zh) | 2018-12-28 | 2018-12-28 | 一种羧基功能化多孔环糊精聚合物及其在吸附和分离溶菌酶中的应用 |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN109589946B (zh) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008137846A3 (en) * | 2007-05-04 | 2009-03-12 | Akermin Inc | Immobilized enzymes and uses thereof |
| CN108314638A (zh) * | 2018-02-06 | 2018-07-24 | 湖南科技大学 | 一种n-二硫代甲酸基-n,n-二乙酸钠螯合剂的制备方法 |
-
2018
- 2018-12-28 CN CN201811627996.3A patent/CN109589946B/zh not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008137846A3 (en) * | 2007-05-04 | 2009-03-12 | Akermin Inc | Immobilized enzymes and uses thereof |
| CN108314638A (zh) * | 2018-02-06 | 2018-07-24 | 湖南科技大学 | 一种n-二硫代甲酸基-n,n-二乙酸钠螯合剂的制备方法 |
Non-Patent Citations (2)
| Title |
|---|
| MAX J. KLEMES等: "Phenolation of cyclodextrin polymers controls their lead and organic micropollutant adsorption", 《CHEMICAL SCIENCE》 * |
| T.S. ANIRUDHAN等: "Adsorptive Separation of Lysozyme from Aqueous Solutions Using Sulphonyl and Carboxyl Functionalized Stearyl Alcohol Grafted Epichlorohydrin", 《J POLYM ENVIRON》 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN109589946B (zh) | 2021-03-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Köse et al. | Applications and impact of nanocellulose based adsorbents | |
| CN109173746A (zh) | 一种高效过滤水中微污染物的复合膜制备方法 | |
| Zhang et al. | Fabrication and bioseparation studies of adsorptive membranes/felts made from electrospun cellulose acetate nanofibers | |
| Duan et al. | Chemically modified kapok fiber for fast adsorption of Pb2+, Cd2+, Cu2+ from aqueous solution | |
| CN102659982B (zh) | 一种黄酮磁性分子印迹聚合物、制备及其在竹叶黄酮分离中的应用 | |
| CN107096514B (zh) | 一种中空结构的硼酸基氧化锡印迹复合纳米微球、其制备方法及其应用 | |
| CN109970912B (zh) | 黄酮类磁性分子印迹聚合物的制备方法 | |
| CN103497276B (zh) | 一种碳纳米管基磁性有机磷分子印迹聚合物的制备方法和应用 | |
| Rahmatika et al. | TEMPO-oxidized cellulose nanofiber (TOCN) decorated macroporous silica particles: Synthesis, characterization, and their application in protein adsorption | |
| CN109174023A (zh) | 一种纳米纤维素交联石墨烯/壳聚糖气凝胶及其制备方法、应用 | |
| CN103278637B (zh) | 一种检测幽门螺旋杆菌的碳纳米管检测试纸及其制备方法 | |
| CN106824099A (zh) | 一种磁性CCPs固相萃取剂及其制备方法和应用 | |
| CN108745321B (zh) | 用于分离花色苷的虚拟模板分子印迹磁性微球的制备方法 | |
| CN103506093A (zh) | 一种磁性双模板蛋白质分子印迹纳米粒子及其制备方法 | |
| CN101864021A (zh) | 一种纳米硅胶表面天麻素分子印迹聚合物的制备方法 | |
| CN113670700B (zh) | 一种富集分离黄曲霉毒素b1的磁性光子晶体微球及其制备方法和应用 | |
| CN101664669A (zh) | 羧基化的单壁碳纳米管-海藻酸固相萃取盘的制备及应用 | |
| CN101880355A (zh) | 一种苏丹红i分子印迹聚合物吸附剂的制备及应用 | |
| JP2017037069A (ja) | 分離剤及びその製造方法、並びに当該分離剤を用いた標的分子の分離方法及びクロマトグラフィー用カラム | |
| CN113893833A (zh) | 一种分子印迹复合二维材料高通量识别黄曲霉毒素的制备方法及其应用 | |
| CN107837796B (zh) | 一种键合型色谱柱固定相 | |
| CN102604008A (zh) | 一种培氟沙星表面分子印迹聚合物的制备方法以及应用 | |
| CN110644137B (zh) | 一种静电纺丝制备微孔复合纳米纤维膜的方法、应用 | |
| CN103044639A (zh) | 一种新型碳纳米管表面分子印迹聚合物及其制备方法 | |
| CN109589946A (zh) | 一种羧基功能化多孔环糊精聚合物及其在吸附和分离溶菌酶中的应用 |
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 | ||
| 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: 20210330 Termination date: 20211228 |