Photocatalytic Decarboxylative Allylation of α-Amino Acids and Peptides under Metal-Free Conditions

Yinlei Zhang; Yanyu Lu; Chengyang Ju; Zhenguo Zhang; Dongping Wang; Shirui Wang; Peizhong Xie; Teck Peng Loh

doi:10.1021/acs.orglett.4c03038

Photocatalytic Decarboxylative Allylation of α-Amino Acids and Peptides under Metal-Free Conditions

Yinlei Zhang, Yanyu Lu, Chengyang Ju, Zhenguo Zhang, Dongping Wang, Shirui Wang, Peizhong Xie, Teck Peng Loh

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

3 Scopus citations

Abstract

We developed an organophotoredox catalytic system to facilitate the decarboxylative allylation coupling process concerning α-amino acids and related C-terminal carboxylate peptides using Morita-Baylis-Hillman adducts as allylic precursors. This metal-free method operates under mild conditions and is compatible with various amino acids. The versatility of this protocol, particularly in chemical biology research, has been preliminarily demonstrated through the ligation of bioactive peptide chains.

Original language	English
Pages (from-to)	8121-8127
Number of pages	7
Journal	Organic Letters
Volume	26
Issue number	38
DOIs	https://doi.org/10.1021/acs.orglett.4c03038
State	Published - 27 Sep 2024
Externally published	Yes

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title = "Photocatalytic Decarboxylative Allylation of α-Amino Acids and Peptides under Metal-Free Conditions",

abstract = "We developed an organophotoredox catalytic system to facilitate the decarboxylative allylation coupling process concerning α-amino acids and related C-terminal carboxylate peptides using Morita-Baylis-Hillman adducts as allylic precursors. This metal-free method operates under mild conditions and is compatible with various amino acids. The versatility of this protocol, particularly in chemical biology research, has been preliminarily demonstrated through the ligation of bioactive peptide chains.",

author = "Yinlei Zhang and Yanyu Lu and Chengyang Ju and Zhenguo Zhang and Dongping Wang and Shirui Wang and Peizhong Xie and Loh, {Teck Peng}",

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year = "2024",

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TY - JOUR

T1 - Photocatalytic Decarboxylative Allylation of α-Amino Acids and Peptides under Metal-Free Conditions

AU - Zhang, Yinlei

AU - Lu, Yanyu

AU - Ju, Chengyang

AU - Zhang, Zhenguo

AU - Wang, Dongping

AU - Wang, Shirui

AU - Xie, Peizhong

AU - Loh, Teck Peng

PY - 2024/9/27

Y1 - 2024/9/27

N2 - We developed an organophotoredox catalytic system to facilitate the decarboxylative allylation coupling process concerning α-amino acids and related C-terminal carboxylate peptides using Morita-Baylis-Hillman adducts as allylic precursors. This metal-free method operates under mild conditions and is compatible with various amino acids. The versatility of this protocol, particularly in chemical biology research, has been preliminarily demonstrated through the ligation of bioactive peptide chains.

AB - We developed an organophotoredox catalytic system to facilitate the decarboxylative allylation coupling process concerning α-amino acids and related C-terminal carboxylate peptides using Morita-Baylis-Hillman adducts as allylic precursors. This metal-free method operates under mild conditions and is compatible with various amino acids. The versatility of this protocol, particularly in chemical biology research, has been preliminarily demonstrated through the ligation of bioactive peptide chains.

UR - http://www.scopus.com/inward/record.url?scp=85204305791&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.4c03038

DO - 10.1021/acs.orglett.4c03038

M3 - 文章

C2 - 39282965

AN - SCOPUS:85204305791

SN - 1523-7060

VL - 26

SP - 8121

EP - 8127

JO - Organic Letters

JF - Organic Letters

IS - 38

ER -

Photocatalytic Decarboxylative Allylation of α-Amino Acids and Peptides under Metal-Free Conditions

Abstract

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