Studies related to the relative thermodynamic stability of C-terminal peptidyl esters of O-hydroxy thiophenol

Emergence of a doable strategy for non-cysteine ligation applicable to the chemical synthesis of glycopeptides

Gong Chen, J. David Warren, Jiehao Chen, Bin Wu, Qian Wan, Samuel J. Danishefsky

Research output: Contribution to journalArticle

51 Citations (Scopus)

Abstract

A pathway has been devised, wherein a phenolic ester of a C-terminal peptide is ligated with an N-terminal peptide through two consecutive acyl migrations. In the first transacylation, the C-terminus is transferred from a phenol to a newly liberated ortho-thiol function. Subsequently, the acyl group is transported to a proximal benzylamine through a six-membered transition state.

Original languageEnglish (US)
Pages (from-to)7460-7462
Number of pages3
JournalJournal of the American Chemical Society
Volume128
Issue number23
DOIs
StatePublished - Jun 14 2006

Fingerprint

Glycopeptides
Thermodynamics
Peptides
Ligation
Esters
Thermodynamic stability
Phenol
Sulfhydryl Compounds
Phenols
thiophenol
calcium ascorbate
benzylamine

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

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abstract = "A pathway has been devised, wherein a phenolic ester of a C-terminal peptide is ligated with an N-terminal peptide through two consecutive acyl migrations. In the first transacylation, the C-terminus is transferred from a phenol to a newly liberated ortho-thiol function. Subsequently, the acyl group is transported to a proximal benzylamine through a six-membered transition state.",
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Studies related to the relative thermodynamic stability of C-terminal peptidyl esters of O-hydroxy thiophenol : Emergence of a doable strategy for non-cysteine ligation applicable to the chemical synthesis of glycopeptides. / Chen, Gong; David Warren, J.; Chen, Jiehao; Wu, Bin; Wan, Qian; Danishefsky, Samuel J.

In: Journal of the American Chemical Society, Vol. 128, No. 23, 14.06.2006, p. 7460-7462.

Research output: Contribution to journalArticle

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AU - Danishefsky, Samuel J.

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