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.
S. Ceretti, G. Luppi, S. De Pol, F. Formaggio, M. Crisma, C. Toniolo, et al. (2004). Total Synthesis of Retro-Peptide Oligomers. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 4188-4196 [10.1002/ejoc.200400242].
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.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
