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