Organic Letters
Organic Letters
5 years ago

Iterative Design of a Biomimetic Catalyst for Amino Acid Thioester Condensation

Iterative Design of a Biomimetic Catalyst for Amino Acid Thioester Condensation
Huabin Wu, Paramjit S. Arora, Monika Raj, Handoko
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.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b02412

DOI: 10.1021/acs.orglett.7b02412

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