THE SOLID-PHASE SYNTHESIS OF N-ALKYLCARBAMATE OLIGOMERS

An efficient method for the solid phase synthesis of N-alkylcarbamate oligomers from alternating carboxylic acid and N-alpha-Fmoc protected chiral p-nitrophenylcarbonate monomers has been developed. The general synthetic scheme involves four steps per coupling cycle: deprotection of the terminal amino group of the growing oligomer, acylation of the free amine with a carboxylic acid monomer, reduction of the resulting amide bond with borane and coupling of the secondary amine to a N-alp ha-Fmoc protected p-nitrophenyl carbonate monomer. This novel biopolym er which has two side chain residues per backbone carbamate linkage an d no backbone hydrogen bond donors may provide new frameworks for drug design as well as folded domains with novel physical and biological p roperties. Copyright (C) 1996 Elsevier Science Ltd