Saturated neoglycopolymers for tissue engineering

Abstract

Norbornene monomers bearing carbohydrate groups of relevance for tissue engineering were synthesized via the norbornene acid chlorides, transformed into their ROMP polymers, and reduced to yield saturated neoglycopolymers. These materials bear either O-glycoside groups designed to cross-link collagen via reaction of the ring-open sugar with free NH2 groups of lysine, or C-glycoside groups. The latter are intended for use as the central block in triblock copolymers terminated with blocks capable of crosslinking: they serve only as potentially biocompatible "spacers" to help span the interlamellar distance in collagen. A third ROMP monomer bearing a succinimide group as an alternative crosslinking agent was also prepared and polymerized. The O-glycoside monomer, bis(1,2;3,4-di-O-isopropylidene-D-galactopyranos-6-O-yl) 5-norbornene-2,3-dicarboxylate 9, and the succinimide monomer, 5-norbornene-2-carboxylic acid N-hydroxysuccinimide ester 11, were prepared by the Diels-Alder synthesis of 5-norbornene-2,3-dicarbonyl chloride 7 and 5-norbornene-2-carboxylic acid chloride 8, and subsequent nucleophilic substitution of the acid chlorides. (Abstract shortened by UMI.)