Iterative design of a biomimetic catalyst for amino acid thioester condensation

Huabin Wu, Handoko, Monika Raj, Paramjit S. Arora

Research output: Contribution to journalArticle

Abstract

Herein, the design of a catalyst that combines lessons learned from peptide biosynthesis, enzymes, and organocatalysts is described. The catalyst features a urea scaffold for carbonyl recognition and elements of nucleophilic catalysis. In the presence of 10 mol % of the organocatalyst, the rate of peptide bond formation is accelerated by 10000-fold over the uncatalyzed reaction between Fmoc-amino acid thioesters and amino acid methyl esters.

Original languageEnglish (US)
Pages (from-to)5122-5125
Number of pages4
JournalOrganic Letters
Volume19
Issue number19
DOIs
StatePublished - Jan 1 2017

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ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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