The first chemical synthesis of novel MeO-3-GlcUA derivative of hyaluronan-based disaccharide to elucidate the catalytic mechanism of hyaluronic acid synthases (HASs)

The first chemical synthesis of MeO-3-GluUA beta(1 -> 3)GlcNAc-UDP to elucidate the catalytic mechanism of hyalyionic acid synthases (HASS) is described. Construction of the desired beta(1 -> 3)-linked disaccharide 10 was achieved very efficiently by Coupling MeO-3-GlcUA donor 3 with the suitable protected GlCnt(10C) acceptor 4 using BF(3) Et(2)O as Lewis acid Chemoselective removal of anomeric NAP, phosphorylation, hydrogenation, coupling with UMP-morpholidate, and finally complete deprotection gave the target compound 1 in good yield (C) 2009 Elsevier Ltd All rights reserved