[go: up one dir, main page]

Hou et al., 2020 - Google Patents

A sulfonium triggered thiol-yne reaction for cysteine modification

Hou et al., 2020

View PDF
Document ID
4288352389632881870
Author
Hou Z
Wang D
Li Y
Zhao R
Wan C
Ma Y
Lian C
Yin F
Li Z
Publication year
Publication venue
The Journal of Organic Chemistry

External Links

Snippet

We report a facile thiol-yne type reaction triggered by the sulfonium center. After facile propargylation of thiolethers, the resulting sulfonium could undergo facile addition with thiols in aqueous media at ambient temperature. Further applying this reaction in unprotected …
Continue reading at hpc.pku.edu.cn (PDF) (other versions)

Classifications

    • GPHYSICS
    • G01MEASURING; TESTING
    • G01NINVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N33/00Investigating or analysing materials by specific methods not covered by the preceding groups
    • G01N33/48Investigating or analysing materials by specific methods not covered by the preceding groups biological material, e.g. blood, urine; Haemocytometers
    • G01N33/50Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
    • G01N33/68Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving proteins, peptides or amino acids
    • G01N33/6803General methods of protein analysis not limited to specific proteins or families of proteins
    • GPHYSICS
    • G01MEASURING; TESTING
    • G01NINVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N33/00Investigating or analysing materials by specific methods not covered by the preceding groups
    • G01N33/48Investigating or analysing materials by specific methods not covered by the preceding groups biological material, e.g. blood, urine; Haemocytometers
    • G01N33/50Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
    • G01N33/53Immunoassay; Biospecific binding assay
    • GPHYSICS
    • G01MEASURING; TESTING
    • G01NINVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N33/00Investigating or analysing materials by specific methods not covered by the preceding groups
    • G01N33/48Investigating or analysing materials by specific methods not covered by the preceding groups biological material, e.g. blood, urine; Haemocytometers
    • G01N33/50Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
    • G01N33/5005Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving human or animal cells
    • GPHYSICS
    • G01MEASURING; TESTING
    • G01NINVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N33/00Investigating or analysing materials by specific methods not covered by the preceding groups
    • G01N33/48Investigating or analysing materials by specific methods not covered by the preceding groups biological material, e.g. blood, urine; Haemocytometers
    • G01N33/50Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
    • G01N33/58Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving labelled substances
    • G01N33/582Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving labelled substances with fluorescent label
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07KPEPTIDES
    • C07K14/00Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
    • C07K14/435Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
    • C07K14/46Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans from vertebrates
    • C07K14/47Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans from vertebrates from mammals
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07KPEPTIDES
    • C07K1/00General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
    • C07K1/107General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length by chemical modification of precursor peptides
    • C07K1/1072General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length by chemical modification of precursor peptides by covalent attachment of residues or functional groups
    • C07K1/1077General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length by chemical modification of precursor peptides by covalent attachment of residues or functional groups by covalent attachment of residues other than amino acids or peptide residues, e.g. sugars, polyols, fatty acids
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07KPEPTIDES
    • C07K7/00Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
    • C07K7/04Linear peptides containing only normal peptide links
    • C07K7/06Linear peptides containing only normal peptide links having 5 to 11 amino acids
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07KPEPTIDES
    • C07K7/00Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
    • C07K7/04Linear peptides containing only normal peptide links
    • C07K7/08Linear peptides containing only normal peptide links having 12 to 20 amino acids
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D207/00Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom

Similar Documents

Publication Publication Date Title
Hou et al. A sulfonium triggered thiol-yne reaction for cysteine modification
Christian et al. A physical organic approach to tuning reagents for selective and stable methionine bioconjugation
Zhang et al. Chemoselective peptide cyclization and bicyclization directly on unprotected peptides
Moiola et al. Stapled peptides—a useful improvement for peptide-based drugs
Tessier et al. “Doubly orthogonal” labeling of peptides and proteins
Lim et al. Photoinducible bioorthogonal chemistry: a spatiotemporally controllable tool to visualize and perturb proteins in live cells
Montgomery et al. Versatile peptide macrocyclization with Diels–Alder cycloadditions
Ma et al. N-Heterocyclic carbene-stabilized palladium complexes as organometallic catalysts for bioorthogonal cross-coupling reactions
Gober et al. Supramolecular affinity labeling of histone peptides containing trimethyllysine and its application to histone deacetylase assays
Li et al. Construction of complex macromulticyclic peptides via stitching with formaldehyde and guanidine
Vamisetti et al. On-demand detachment of succinimides on cysteine to facilitate (semi) synthesis of challenging proteins
West et al. Design and evaluation of a cyclobutane diazirine alkyne tag for photoaffinity labeling in cells
Gui et al. Photocaged cell-permeable ubiquitin probe for temporal profiling of deubiquitinating enzymes
Islam et al. Unprotected peptide macrocyclization and stapling via a fluorine-thiol displacement reaction
Zhang et al. Site-selective lysine reactions guided by protein–peptide interaction
Stefanucci et al. Fluorescent-labeled bioconjugates of the opioid peptides biphalin and DPDPE incorporating fluorescein–maleimide linkers
Peran et al. General strategy for the bioorthogonal incorporation of strongly absorbing, solvation-sensitive infrared probes into proteins
Garrigou et al. Accelerated identification of cell active KRAS inhibitory macrocyclic peptides using mixture libraries and automated ligand identification system (ALIS) technology
Wan et al. Electrophilic sulfonium-promoted peptide and protein amidation in aqueous media
Gao et al. Thioether-bonded fluorescent probes for deciphering thiol-mediated exchange reactions on the cell surface
Brown et al. Multiple synthetic routes to the mini-protein omomyc and coiled-coil domain truncations
Chen et al. Non-symmetric stapling of native peptides
Wu et al. Fast and selective reaction of 2-benzylacrylaldehyde with 1, 2-aminothiol for stable N-terminal cysteine modification and peptide cyclization
Liu et al. Synthesis of fluorescent cyclic peptides via gold (I)-catalyzed macrocyclization
Bao et al. Visible-light mediated deoxygenation of carboxylic acid for late-stage peptide modification targeting dehydroalanine