Efficient and selective syntheses of S -Acyl and N -Acyl glutathiones

Alan R. Katritzky, Nader E. Abo- Dya, Srinivasa R. Tala, Ebrahim H. Ghazvini-Zadeh, Kiran Bajaj, Said A. El-Feky

Research output: Contribution to journalArticlepeer-review

10 Scopus citations

Abstract

Selective syntheses of S-acyl glutathiones are achieved in 79-98% yields using 1-acyl-1H-benzotriazoles in the presence of potassium bicarbonate in aqueous methanol at 20C. N-Acylation of S-(p-nitrobenzoyl) glutathione with 1-acyl-1H-benzotriazoles followed by deprotection of the p-nitrobenzoyl groups under mild conditions gave 63-78% yields of N-acyl glutathiones. These methodologies should be useful for the S-acylation and N-acylation of peptides and glycopeptides.

Original languageEnglish (US)
Pages (from-to)1337-1340
Number of pages4
JournalSynlett
Issue number9
DOIs
StatePublished - Jun 14 2010

Keywords

  • Acylation
  • Amino acids
  • Drugs
  • Glutathione
  • Peptides

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