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, cilt.78, sa.8, ss.3541-3552, 2013 (SCI-Expanded) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 78 Sayı: 8
  • Basım Tarihi: 2013
  • Doi Numarası: 10.1021/jo302251e
  • Dergi Adı: JOURNAL OF ORGANIC CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Index Chemicus (IC), Current Chemical Reactions (CCR)
  • Sayfa Sayıları: ss.3541-3552
  • Anadolu Üniversitesi Adresli: Evet

Özet

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.