Iterative design of a biomimetic catalyst for amino acid thioester condensation

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

doi:10.1021/acs.orglett.7b02412

Iterative design of a biomimetic catalyst for amino acid thioester condensation

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

Chemistry

Research output: Contribution to journal › Article › peer-review

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 language	English (US)
Pages (from-to)	5122-5125
Number of pages	4
Journal	Organic Letters
Volume	19
Issue number	19
DOIs	https://doi.org/10.1021/acs.orglett.7b02412
State	Published - Oct 6 2017

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.7b02412

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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.",

author = "Huabin Wu and Handoko and Monika Raj and Arora, {Paramjit S.}",

note = "Funding Information: We thank the U.S. National Science Foundation (CHE-1506854) for financial support of this work. Publisher Copyright: {\textcopyright} 2017 American Chemical Society.",

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AU - Arora, Paramjit S.

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Iterative design of a biomimetic catalyst for amino acid thioester condensation

Abstract

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