4.8 Article

Biocompatible Photoinduced Alkylation of Dehydroalanine for the Synthesis of Unnatural α-Amino Acids

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ORGANIC LETTERS
卷 23, 期 13, 页码 5251-5255

出版社

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c01781

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资金

  1. INCT-Catalise/CNPq [444061/2018-5]
  2. FAPESP [14/50249-8, 19/01973-9, 17/10015-6]
  3. GSK
  4. Coordenacao de Aperfeicoamento de Pessoal de Nivel Superior-Brasil (CAPES) [001]

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This technology utilizes alkyl radicals to selectively alkylate dehydroalanine, offering a convenient method for the synthesis of unnatural amino acids and late-stage functionalization of pharmaceuticals.
A site-selective alkylation of dehydroalanine to access protected unnatural amino acids is described. The protocol is characterized by the wide nature of alkyl radicals employed, mild conditions, and functional group compatibility. This protocol is further extended to access peptides, late-stage functionalization of pharmaceuticals, and enantioenriched amino acids.

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