An unsaturated peptidomimetic assembly derived from a carbohydrate

A strategy has been established for the synthesis of peptidomimetics derived from unsaturated carbohydrates, and exemplified by the use of methyl 2,6‐anhydro‐7‐azido‐3,7‐deoxy‐4,5‐ O ‐isopropylidene‐ D ‐ lyxo ‐hept‐2‐enonate 9 as a dipeptide ‘monomer’ which can be elaborated from either end. Selective reduction of 9 gives a protected pseudodipeptide ester suitable for use as an amino component, and saponification gives an azido acid suitable for use as a carboxyl component. The ‘dimer’ product of coupling these two components with TBTU can be similarly elaborated at either end to give a ‘trimer’, and a further cycle of selective reduction and coupling gave a ‘tetramer’, 17 , a pseudo‐octapeptide. Copyright © 2003 European Peptide Society and John Wiley & Sons, Ltd.