Iterative design of a biomimetic catalyst for amino acid thioester condensation

Huabin Wu, Handoko, Monika Raj, Paramjit 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 - 2017

Fingerprint

Biomimetics
biomimetics
peptides
amino acids
Condensation
Peptide Biosynthesis
condensation
Amino Acids
catalysts
Peptides
Catalysts
biosynthesis
lessons learned
Biosynthesis
Catalysis
ureas
Scaffolds
catalysis
Urea
enzymes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Iterative design of a biomimetic catalyst for amino acid thioester condensation. / Wu, Huabin; Handoko; Raj, Monika; Arora, Paramjit.

In: Organic Letters, Vol. 19, No. 19, 2017, p. 5122-5125.

Research output: Contribution to journalArticle

Wu, Huabin ; Handoko ; Raj, Monika ; Arora, Paramjit. / Iterative design of a biomimetic catalyst for amino acid thioester condensation. In: Organic Letters. 2017 ; Vol. 19, No. 19. pp. 5122-5125.
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