The total synthesis of sequential oligomers of retro-peptides of the general formula Boc(-gGly-mAib)(n)-OBn, starting from dimethylmalonic acid, has been carried out in good overall yield. The key step is the formation of the gGly unit >N-CH2-N<, which is easily obtained in a one-pot/threestep reaction from BnO-mAib-Gly-OH and 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 sequential retro-peptide oligomers
FORMAGGIO, FERNANDO;TONIOLO, CLAUDIO;
2004
Abstract
The total synthesis of sequential oligomers of retro-peptides of the general formula Boc(-gGly-mAib)(n)-OBn, starting from dimethylmalonic acid, has been carried out in good overall yield. The key step is the formation of the gGly unit >N-CH2-N<, which is easily obtained in a one-pot/threestep reaction from BnO-mAib-Gly-OH and 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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