Benzotriazole-Mediated Synthesis of Aza-peptides: En Route to an Aza-Leuenkephalin Analogue

Abo-Dya N. E., Biswas S., Basak A., Avan I., Alamry K. A., Katritzky A. R.

JOURNAL OF ORGANIC CHEMISTRY, vol.78, no.8, pp.3541-3552, 2013 (SCI-Expanded) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 78 Issue: 8
  • Publication Date: 2013
  • Doi Number: 10.1021/jo302251e
  • Journal Name: JOURNAL OF ORGANIC CHEMISTRY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Index Chemicus (IC), Current Chemical Reactions (CCR)
  • Page Numbers: pp.3541-3552
  • Anadolu University Affiliated: Yes

Abstract

Novel N-(N-Pg-azadipeptidoyl)benzotriazoles 20a-e couple efficiently with alpha-amino acids 21a-e, dipeptides 22a-c, aminoxyacetic acid 23a, depsidipeptide 23b, and alpha-hydroxy-beta-phenylpropionic acid 27 yielding, respectively, azatripeptides 24a-g, azatetrapeptides 25a,b, a hybrid azatripeptide with an oxyamide bond 26a, a hybrid azatetrapeptide with an ester bond 26b, and a hybrid azatripeptide with an ester bond 28. A new protocol for the synthesis of N-Pg-azatripeptides 33a,b and 35a,b, each containing a natural amino acid at the N-terminus, avoids the low coupling rates of the aza-amino acid residue and enables the solution-phase synthesis of an azaphenylalanine analogue of Leu-enkephalin 40.