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^*

^*Corresponding author for this work

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

3 Citations (Scopus)

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
Journal	Organic Letters
DOIs	https://doi.org/10.1021/acs.orglett.4c03038
Publication status	Accepted/In press - 2024
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2024 American Chemical Society.

ASJC Scopus Subject Areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1021/acs.orglett.4c03038

Cite this

@article{23a36544b69e44c8972b645e291c8c43,

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\}",

note = "Publisher Copyright: {\textcopyright} 2024 American Chemical Society.",

year = "2024",

doi = "10.1021/acs.orglett.4c03038",

language = "English",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

}

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

Y1 - 2024

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

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

U2 - 10.1021/acs.orglett.4c03038

DO - 10.1021/acs.orglett.4c03038

M3 - Article

AN - SCOPUS:85204305791

SN - 1523-7060

JO - Organic Letters

JF - Organic Letters

ER -

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

Abstract

Bibliographical note

ASJC Scopus Subject Areas

Access to Document

Other files and links

Fingerprint

Cite this