Peptidyl Thiophenols as Substrates for Nonribosomal Peptide Cyclases

Stephan A. Sieber, Junhua Tao, Christopher T. Walsh, Mohamed A. Marahiel

Research output: Contribution to journalArticlepeer-review

55 Scopus citations

Abstract

Activity-based enzyme acylation: Although small peptides are specifically cyclized by nonribosomal peptide cyclases (thioesterases, TEs) in nature, artificial N-acetylcysteamine thioester (SNAC) mimics have often failed to act as substrates for these enzymes in vitro. However, new reactive peptidyl aromatic thioesters solve this problem by selective acylation of the enzyme active site (see scheme).

Original languageEnglish
Pages (from-to)493-498
Number of pages6
JournalAngewandte Chemie International Edition in English
Volume43
Issue number4
DOIs
StatePublished - 16 Jan 2004
Externally publishedYes

Keywords

  • Antibiotics
  • Biomimetic synthesis
  • Cyclization
  • Enzyme catalysis
  • Peptides

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