Benzotriazole reagents for the syntheses of Fmoc-, Boc-, and Alloc-protected amino acids

Tarek S. Ibrahim, Srinivasa R. Tala, Said A. El-Feky, Zakaria K. Abdel-Samii, Alan R. Katritzky

Research output: Contribution to journalArticlepeer-review

9 Scopus citations

Abstract

Stable Fmoc-, Boc-, and Alloc-benzotriazoles react with various amino acids including unprotected serine and glutamic acid, in the presence of triethylamine at 20° as reagents to introduce -amino protecting groups to afford Fmoc-, Boc-, and Alloc-protected amino acids (77-94%) free of dipeptide and tripeptide impurities. Fmoc-, and Alloc-Gly-Gly-OH dipeptides were prepared in 90% yields by N-acylation of glycylglycine with Fmoc- and Alloc-benzotriazoles in the presence of triethylamine. Synthesized N-protected amino acids were greater than 99% pure, analyzed by HPLC.

Original languageEnglish (US)
Article numberS03511ST
Pages (from-to)2013-2016
Number of pages4
JournalSynlett
Issue number14
DOIs
StatePublished - Aug 11 2011

Keywords

  • HPLC
  • acylation
  • amino acids
  • benzotriazole
  • protecting groups

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