Photocatalyzed Oxidative Decarboxylation Forming Aminovinylcysteine Containing Peptides †

Masaya Kumashiro, Kosuke Ohsawa, Takayuki Doi

Research output: Contribution to journalArticlepeer-review

Abstract

The formation of (2S,3S)-S-[(Z)-aminovinyl]-3-methyl-D-cysteine (AviMeCys) substructures was developed based on the photocatalyzed-oxidative decarboxylation of lanthionine-bearing peptides. The decarboxylative selenoetherification of the N-hydroxyphthalimide ester, generated in situ, proceeded under mild conditions at −40 °C in the presence of 1 mol% of eosin Y-Na2 as a photocatalyst and the Hantzsch ester. The following β-elimination of the corresponding N,Se-acetal was operated in a one-pot operation, led to AviMeCys substructures found in natural products in moderate to good yields. The sulfide-bridged motif, and also the carbamate-type protecting groups, such as Cbz, Teoc, Boc and Fmoc groups, were tolerant under the reaction conditions.

Original languageEnglish
Article number1615
JournalCatalysts
Volume12
Issue number12
DOIs
Publication statusPublished - 2022 Dec

Keywords

  • (2S,3S)-S-[(Z)-aminovinyl]-3-methyl-D-cysteine (AviMeCys)
  • Eosin Y
  • N-hydroxyphthalimide (NHPI) ester
  • oxidative decarboxylation
  • photocatalytic reaction
  • ribosomally synthesized and post-translationally modified peptides (RiPPs)
  • β-thioenamide

ASJC Scopus subject areas

  • Catalysis
  • Environmental Science(all)
  • Physical and Theoretical Chemistry

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