Arabinose-derived bicyclic amino acids: synthesis, conformational analysis and construction of an αvβ3-selective RGD peptide

Abstract

The synthesis, NMR structure determination, and molecular modelling of the conformationally restricted diastereomeric sugar azido acids 1 and 2 are presented. The bicyclic structures of these compounds are obtained through a iodocyclization reaction on the C-allyl glycoside of the D-arabinofuranose. Cyclic tetrapeptide 11 containing the amino acid derived from 1 linked to the RGD sequence has been synthesized; this compound was found to be a selective antagonist of α_vβ₃ integrins expressed on GM 7373 cells.