Shyam M. Rele

Design and synthesis of hyaluronan-mimetic gemini disaccharides

An efficient strategy has been designed for the preparation of synthetic mimics of hyaluronan (HA, 1) and its dimerized (Gemini) disaccharides (2a,b) via n-pentenyl glycoside formation. Construction of the target molecules was achieved through a combination of protection/deprotection protocols, imidate glycosylation methodology followed by ozonolysis, and reductive amination. These tailored synthetic mimics could act as versatile building blocks with therapeutic applications in tissue engineering, treatment of cancer and as drug delivery agents.

Homodimerization of hyaluronan and heparan sulfate derivatives by olefin metathesis reaction

Abstract Hyaluronan and heparan sulfate disaccharides of the type β- d -glucuronic acid-(1→3)- N -acetyl-β- d -glucosamine and α- l -iduronic acid-(1→4)- N -acetyl-β- d -glucosamine, respectively, with an n -pentenyl group at the reducing end have been synthesized. Homodimerization of these derivatives using Grubbs catalyst furnished dimerized disaccharides separated by a C 8 spacer arm.

Synthesis of a hyaluronan neoglycopolymer by ring-opening metathesis polymerization.

A hyaluronan (HA)-derived disaccharide was synthesized bearing an n-pentenyl spacer arm, which facilitated disaccharide derivatization with a norbornene template. Subsequent ring opening metathesis polymerization of the monomer produced an HA-mimetic neoglycopolymer of low polydispersity.