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.File in questo prodotto:
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