title: The first chemical synthesis of novel MeO-3-GlcUA derivative of hyaluronan-based disaccharide to elucidate the catalytic mechanism of hyaluronic acid synthases (HASs).
abstract: The first chemical synthesis of MeO-3-GlcUAβ(1→3)GlcNAc-UDP to elucidate the catalytic mechanism of hyaluronic acid synthases (HASs) is described. Construction of the desired β(1→3)-linked disaccharide 10 was achieved very efficiently by coupling MeO-3-GlcUA donor 3 with the suitable protected GlcNTroc 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.
authors.affiliation: Cancer Biology, Roswell Park Cancer Institute, Buffalo, NY 14263, USA.
authors.forename: Guohua
authors.initials: G
authors.lastname: Wei
authors.forename: Vipin
authors.initials: V
authors.lastname: Kumar
authors.forename: Jun
authors.initials: J
authors.lastname: Xue
authors.forename: Robert D
authors.initials: RD
authors.lastname: Locke
authors.forename: Khushi L
authors.initials: KL
authors.lastname: Matta