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Chemoselective Peptide Modification via Photocatalytic Tryptophan ß-Position Conjugation.
Yu, Younong; Zhang, Li-Kang; Buevich, Alexei V; Li, Guoqing; Tang, Haiqun; Vachal, Petr; Colletti, Steven L; Shi, Zhi-Cai.
Afiliação
  • Yu Y; Department of Discovery Chemistry , MRL, Merck & Co., Inc. , Kenilworth , New Jersey 07033 , United States.
  • Zhang LK; Department of Process Research and Development , Merck & Co., Inc. , Rahway , New Jersey 07065 , United States.
  • Buevich AV; Department of Process Research and Development , Merck & Co., Inc. , Rahway , New Jersey 07065 , United States.
  • Li G; Department of Discovery Chemistry , MRL, Merck & Co., Inc. , Kenilworth , New Jersey 07033 , United States.
  • Tang H; Department of Discovery Chemistry , MRL, Merck & Co., Inc. , Kenilworth , New Jersey 07033 , United States.
  • Vachal P; Department of Discovery Chemistry , MRL, Merck & Co., Inc. , Kenilworth , New Jersey 07033 , United States.
  • Colletti SL; Department of Discovery Chemistry , MRL, Merck & Co., Inc. , Kenilworth , New Jersey 07033 , United States.
  • Shi ZC; Department of Discovery Chemistry , MRL, Merck & Co., Inc. , Kenilworth , New Jersey 07033 , United States.
J Am Chem Soc ; 140(22): 6797-6800, 2018 06 06.
Article em En | MEDLINE | ID: mdl-29762027
Targeting tryptophan is a promising strategy to achieve high levels of selectivity for peptide or protein modification. A chemoselective peptide modification method via photocatalytic tryptophan ß-position conjugation has been discovered. This transformation has good substrate scope for both peptide and Michael acceptor, and has good chemoselectivity versus other amino acid residues. The endogenous peptides, glucagon and GLP-1 amide, were both successfully conjugated at the tryptophan ß-position. Insulin was studied as a nontryptophan control molecule, resulting in exclusive B-chain C-terminal-selective decarboxylative conjugation. This transformation provides a novel approach toward peptide modification to support the discovery of new therapeutic peptides, protein labeling and bioconjugation.
Assuntos

Texto completo: 1 Base de dados: MEDLINE Assunto principal: Peptídeos / Triptofano / Proteínas / Processos Fotoquímicos Idioma: En Ano de publicação: 2018 Tipo de documento: Article

Texto completo: 1 Base de dados: MEDLINE Assunto principal: Peptídeos / Triptofano / Proteínas / Processos Fotoquímicos Idioma: En Ano de publicação: 2018 Tipo de documento: Article