Iterative Design of a Biomimetic Catalyst for Amino Acid Thioester Condensation

作者:Wu Huabin; Handoko; Raj Monika; Arora Paramjit S*
来源:Organic Letters, 2017, 19(19): 5122-5125.
DOI:10.1021/acs.orglett.7b02412

摘要

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 40 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.

  • 出版日期2017-10-6