The total synthesis of sequential oligomers of the retro peptides having the general formula Boc-(gGly-mAib)n-OBn has been carried out starting from dimethyl malonic acid in good overall yield. The key step is the formation of the gGly unit, which is easily obtained in a one pot - three steps reaction from BnO-mAib-Gly-OH with diphenylphosphoryl azide. The synthesis of the sequential oligomers of RCO-(gAla-mAib)n-OR’ was also attempted, but the oligomerization step failed, because the gAla moiety readily decomposes or racemizes.

Total Synthesis of Retro-Peptide Oligomers

LUPPI, GIANLUIGI;TOMASINI, CLAUDIA
2004

Abstract

The total synthesis of sequential oligomers of the retro peptides having the general formula Boc-(gGly-mAib)n-OBn has been carried out starting from dimethyl malonic acid in good overall yield. The key step is the formation of the gGly unit, which is easily obtained in a one pot - three steps reaction from BnO-mAib-Gly-OH with diphenylphosphoryl azide. The synthesis of the sequential oligomers of RCO-(gAla-mAib)n-OR’ was also attempted, but the oligomerization step failed, because the gAla moiety readily decomposes or racemizes.
2004
S. Ceretti; G. Luppi; S. De Pol; F. Formaggio; M. Crisma; C. Toniolo; C. Tomasini
File in questo prodotto:
Eventuali allegati, non sono esposti

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11585/18763
 Attenzione

Attenzione! I dati visualizzati non sono stati sottoposti a validazione da parte dell'ateneo

Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 9
  • ???jsp.display-item.citation.isi??? 9
social impact