Photocatalytic decarboxylative allylation of α-amino acids and peptides under metal-free conditions

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...

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Main Authors:	Zhang, Yinlei, Lu, Yanyu, Ju, Chengyang, Zhang, Zhenguo, Wang, Dongping, Wang, Shirui, Xie, Peizhong, Loh, Teck-Peng
Other Authors:	School of Physical and Mathematical Sciences
Format:	Article
Language:	English
Published:	2024
Subjects:	Chemistry Allyl compound Amino acid
Online Access:	https://hdl.handle.net/10356/181037
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Institution:	Nanyang Technological University
Language:	English

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spelling	sg-ntu-dr.10356-1810372024-11-12T02:10:51Z Photocatalytic decarboxylative allylation of α-amino acids and peptides under metal-free conditions Zhang, Yinlei Lu, Yanyu Ju, Chengyang Zhang, Zhenguo Wang, Dongping Wang, Shirui Xie, Peizhong Loh, Teck-Peng School of Physical and Mathematical Sciences Chemistry Allyl compound Amino acid 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. Agency for Science, Technology and Research (ASTAR) Nanyang Technological University The authors gratefully acknowledge the financial support from the National Natural Science Foundation of China (21702108), the Natural Science Foundation of Jiangsu Province, China (BK20211257), the Six Talent Peaks Project in Jiangsu Province (YY-033), a Distinguished University Professor Grant (Nanyang Technological University), and the Agency for Science, Technology, and Research (ASTAR) under its MTC Individual Research Grant (M21K2c0114) and RIE2025 MTC Programmatic Fund (M22K9b0049) for T.-P.L. 2024-11-12T02:10:51Z 2024-11-12T02:10:51Z 2024 Journal Article Zhang, Y., Lu, Y., Ju, C., Zhang, Z., Wang, D., Wang, S., Xie, P. & Loh, T. (2024). Photocatalytic decarboxylative allylation of α-amino acids and peptides under metal-free conditions. Organic Letters, 26(38), 8121-8127. https://dx.doi.org/10.1021/acs.orglett.4c03038 1523-7060 https://hdl.handle.net/10356/181037 10.1021/acs.orglett.4c03038 39282965 2-s2.0-85204305791 38 26 8121 8127 en M21K2c0114 M22K9b0049 Organic Letters © 2024 American Chemical Society. All rights reserved.
institution	Nanyang Technological University
building	NTU Library
continent	Asia
country	Singapore Singapore
content_provider	NTU Library
collection	DR-NTU
language	English
topic	Chemistry Allyl compound Amino acid
spellingShingle	Chemistry Allyl compound Amino acid Zhang, Yinlei Lu, Yanyu Ju, Chengyang Zhang, Zhenguo Wang, Dongping Wang, Shirui Xie, Peizhong Loh, Teck-Peng Photocatalytic decarboxylative allylation of α-amino acids and peptides under metal-free conditions
description	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.
author2	School of Physical and Mathematical Sciences
author_facet	School of Physical and Mathematical Sciences Zhang, Yinlei Lu, Yanyu Ju, Chengyang Zhang, Zhenguo Wang, Dongping Wang, Shirui Xie, Peizhong Loh, Teck-Peng
format	Article
author	Zhang, Yinlei Lu, Yanyu Ju, Chengyang Zhang, Zhenguo Wang, Dongping Wang, Shirui Xie, Peizhong Loh, Teck-Peng
author_sort	Zhang, Yinlei
title	Photocatalytic decarboxylative allylation of α-amino acids and peptides under metal-free conditions
title_short	Photocatalytic decarboxylative allylation of α-amino acids and peptides under metal-free conditions
title_full	Photocatalytic decarboxylative allylation of α-amino acids and peptides under metal-free conditions
title_fullStr	Photocatalytic decarboxylative allylation of α-amino acids and peptides under metal-free conditions
title_full_unstemmed	Photocatalytic decarboxylative allylation of α-amino acids and peptides under metal-free conditions
title_sort	photocatalytic decarboxylative allylation of α-amino acids and peptides under metal-free conditions
publishDate	2024
url	https://hdl.handle.net/10356/181037
_version_	1816859015227899904

Photocatalytic decarboxylative allylation of α-amino acids and peptides under metal-free conditions

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