Literature DB >> 32109071

Access to Unnatural α-Amino Acids via Visible-Light-Mediated Decarboxylative Conjugate Addition to Dehydroalanine.

Akshay A Shah1, Michael J Kelly1, James J Perkins1.   

Abstract

An expedient synthesis of β-alkyl α-amino acids is reported via application of decarboxylative photocatalysis. The method utilizes abundant, diverse, and inexpensive carboxylic acids to provide radicals for conjugate addition to dehydroalanine ester. High-throughput experimentation revealed an acridinium-based photocatalyst, tetraMeO-Acri-N-diMeOPh, to be the optimal choice enabling a general method that is tolerant to a wide range of functional groups. A scalable batch protocol and a parallel library synthesis for accessing diverse unnatural α-amino acids are described.

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Year:  2020        PMID: 32109071     DOI: 10.1021/acs.orglett.0c00371

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  4 in total

1.  carba-Nucleopeptides (cNPs): A Biopharmaceutical Modality Formed through Aqueous Rhodamine B Photoredox Catalysis.

Authors:  Jacob R Immel; Steven Bloom
Journal:  Angew Chem Int Ed Engl       Date:  2022-05-17       Impact factor: 16.823

2.  Combining flavin photocatalysis with parallel synthesis: a general platform to optimize peptides with non-proteinogenic amino acids.

Authors:  Jacob R Immel; Maheshwerreddy Chilamari; Steven Bloom
Journal:  Chem Sci       Date:  2021-06-30       Impact factor: 9.969

3.  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

Review 4.  Radical-Based Synthesis and Modification of Amino Acids.

Authors:  Francisco José Aguilar Troyano; Kay Merkens; Khadijah Anwar; Adrián Gómez-Suárez
Journal:  Angew Chem Int Ed Engl       Date:  2020-11-04       Impact factor: 15.336

  4 in total

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