Rapid Electrophilic Cysteine Arylation with Pyridinium Salts.

Cysteine / chemistry Salts Proteins / chemistry Peptides / chemistry Indicators and Reagents

Journal

Bioconjugate chemistry
ISSN: 1520-4812
Titre abrégé: Bioconjug Chem
Pays: United States
ID NLM: 9010319

Informations de publication

Date de publication:
16 11 2022
Historique:
pubmed: 7 11 2022
medline: 19 11 2022
entrez: 6 11 2022
Statut: ppublish

Résumé

Here, we present a series of fluorinated cationic reagents that enable rapid arylation of cysteine under mild conditions compatible with proteins and peptides. The highly polarized C-F bond and attractive nucleophile-electrophile Coulombic interactions substantially accelerate cysteine arylation, leading to unusually high rate constants on the order of 100 M

Identifiants

DOI: 10.1021/acs.bioconjchem.2c00419 PMID: 36335596
pubmed: 36335596
doi: 10.1021/acs.bioconjchem.2c00419
doi:

Substances chimiques

Cysteine K848JZ4886
Salts 0
Proteins 0
Peptides 0
Indicators and Reagents 0

Types de publication

Journal Article Research Support, U.S. Gov't, Non-P.H.S. Research Support, N.I.H., Extramural

Langues

eng

Sous-ensembles de citation

IM

Pagination

2189-2196

Subventions

Organisme : NIGMS NIH HHS
ID : P20 GM103430
Pays : United States

Auteurs

Bradley M Lipka (BM)

Department of Chemistry, University of Rhode Island, 140 Flagg Road, Kingston, Rhode Island02881, United States.

Vincent M Betti (VM)

Department of Chemistry, Colgate University, 13 Oak Drive, Hamilton, New York13346, United States.
ORCID: 0000-0003-0124-6793

Daniel S Honeycutt (DS)

Department of Chemistry, University of Rhode Island, 140 Flagg Road, Kingston, Rhode Island02881, United States.
ORCID: 0000-0001-6143-4492

Daniel L Zelmanovich (DL)

Department of Chemistry, Colgate University, 13 Oak Drive, Hamilton, New York13346, United States.

Max Adamczyk (M)

Department of Chemistry, University of Rhode Island, 140 Flagg Road, Kingston, Rhode Island02881, United States.

Ruojun Wu (R)

Department of Chemistry, Colgate University, 13 Oak Drive, Hamilton, New York13346, United States.
ORCID: 0000-0003-0097-6698

Harrison S Blume (HS)

Department of Chemistry, Colgate University, 13 Oak Drive, Hamilton, New York13346, United States.
ORCID: 0000-0003-0557-7821

Caitlin A Mendina (CA)

Department of Chemistry, Colgate University, 13 Oak Drive, Hamilton, New York13346, United States.

Jacob M Goldberg (JM)

Department of Chemistry, Colgate University, 13 Oak Drive, Hamilton, New York13346, United States.
ORCID: 0000-0002-8004-3769

Fang Wang (F)

Department of Chemistry, University of Rhode Island, 140 Flagg Road, Kingston, Rhode Island02881, United States.
ORCID: 0000-0002-9192-6858

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Classifications MeSH

questionsmedicales.fr › Acides aminés, peptides et protéines › Acides aminés › Acides aminés soufrés › Cystéine › Rapid Electrophilic Cysteine Arylation with...
questionsmedicales.fr › Produits chimiques inorganiques › Sels › Rapid Electrophilic Cysteine Arylation with...
questionsmedicales.fr › Acides aminés, peptides et protéines › Protéines › Rapid Electrophilic Cysteine Arylation with...
questionsmedicales.fr › Acides aminés, peptides et protéines › Peptides › Rapid Electrophilic Cysteine Arylation with...
questionsmedicales.fr › Actions chimiques et utilisations › Utilisations spécialisées de produits chimiques › Produits chimiques de laboratoire › Indicateurs et réactifs › Rapid Electrophilic Cysteine Arylation with...