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

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

14 Scopus citations

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
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 - 6 Oct 2017
Externally published	Yes

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title = "Iterative design of a biomimetic catalyst for amino acid thioester condensation",

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 = "Publisher Copyright: {\textcopyright} 2017 American Chemical Society.",

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doi = "10.1021/acs.orglett.7b02412",

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AU - Wu, Huabin

AU - Handoko,

AU - Raj, Monika

AU - Arora, Paramjit S.

PY - 2017/10/6

Y1 - 2017/10/6

N2 - 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.

AB - 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.

UR - https://www.scopus.com/pages/publications/85032646813

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DO - 10.1021/acs.orglett.7b02412

M3 - Article

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VL - 19

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EP - 5125

JO - Organic Letters

JF - Organic Letters

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ER -

Iterative design of a biomimetic catalyst for amino acid thioester condensation

Abstract

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