A SOLID-PHASE APPROACH TO OLIGOMERS OF CARBOHYDRATE AMINO-ACIDS - SECONDARY STRUCTURE IN A TRIMERIC FURANOSE CARBOPEPTOID

The synthesis of oligomers of a C-arabinofuranosyl carbohydrate amino acid on a polystyrene support functionalised with a Pink linker is rep orted. Cleavage from the solid support gives ready access to dimeric a nd trimeric carbopeptoids bearing a C-terminal carboxamide. Investigat ions into the solution structure of these novel carbopeptoids utilisin g H-1 NMR indicate that they adopt well defined conformations based ar ound a repeating beta-turn like structure stabilised by (i, i-2) inter -residue hydrogen bonds. (C) 1998 Elsevier Science Ltd. All rights res erved.