Literature DB >> 30296349

Visible-Light-Driven, Copper-Catalyzed Decarboxylative C(sp3 )-H Alkylation of Glycine and Peptides.

Chao Wang1, Mengzhun Guo1, Rupeng Qi1, Qinyu Shang1, Qiang Liu2, Shan Wang1, Long Zhao1, Rui Wang1, Zhaoqing Xu1.   

Abstract

Despite a well-developed and growing body of work in Cu catalysis, the potential of Cu to serve as a photocatalyst remains underexplored. Reported herein is the first example of visible-light-induced Cu-catalyzed decarboxylative C(sp3 )-H alkylation of glycine for preparing α-alkylated unnatural α-amino acids. It merits mentioning that the mild conditions and the good functional-group tolerance allow the modification of peptides using this method. The mechanistic studies revealed that a radical-radical coupling pathway is involved in the reaction.
© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  copper; cross-coupling; peptides; photochemistry; radicals

Mesh:

Substances:

Year:  2018        PMID: 30296349     DOI: 10.1002/anie.201809400

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  4 in total

Review 1.  Recent advances in photocatalyzed reactions using well-defined copper(I) complexes.

Authors:  Mingbing Zhong; Xavier Pannecoucke; Philippe Jubault; Thomas Poisson
Journal:  Beilstein J Org Chem       Date:  2020-03-23       Impact factor: 2.883

2.  Visible-light-mediated catalyst-free synthesis of unnatural α-amino acids and peptide macrocycles.

Authors:  Mengran Wang; Chao Wang; Yumei Huo; Xiaobo Dang; Hongxiang Xue; Liangyu Liu; Hongli Chai; Xiuling Xie; Zhixuan Li; Doudou Lu; Zhaoqing Xu
Journal:  Nat Commun       Date:  2021-11-25       Impact factor: 14.919

3.  Preparation of α-amino acids via Ni-catalyzed reductive vinylation and arylation of α-pivaloyloxy glycine.

Authors:  Xianghua Tao; Yanchi Chen; Jiandong Guo; Xiaotai Wang; Hegui Gong
Journal:  Chem Sci       Date:  2020-10-27       Impact factor: 9.825

Review 4.  Recent Advances in Rapid Synthesis of Non-proteinogenic Amino Acids from Proteinogenic Amino Acids Derivatives via Direct Photo-Mediated C-H Functionalization.

Authors:  Zhenbo Yuan; Xuanzhong Liu; Changmei Liu; Yan Zhang; Yijian Rao
Journal:  Molecules       Date:  2020-11-12       Impact factor: 4.411

  4 in total

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