title: Synthesis of core-class 2 O-linked glycopeptides: a benzyl-protected tetrasaccharyl serine and its derivative carrying a hydrophobic cholestanyl group.
abstract: A core-class 2 tetrasaccharide-linked serine was synthesized in a convergent manner. The coupling reaction of disaccharide glycosyl donor 3 and acceptor 4 stereoselectively afforded tetrasaccharide 15, which was converted to glycosyl fluoride 20. Glycosylation of Fmoc serine allyl ester 5 with 20 produced alpha- and beta-glycosides in 40% and 33% yields, respectively. Alpha-Isomer 21 was converted into 1, a useful building block for the solid-phase synthesis of glycopeptides. On the other hand, 21 was N-deprotected and condensed with hydrophobic cholestanol through a succinyl spacer. The same compound was alternatively synthesized by coupling 20 and 28. Functional group manipulation and hydrogenation afforded core 2 tetrasaccharide-cholestanol conjugate 2.
authors.affiliation: Institute of Glycotechnology, Department of Applied Biochemistry, Tokai University, Hiratsuka-shi, Kanagawa, Japan.
authors.forename: Jun
authors.initials: J
authors.lastname: Watabe
authors.forename: Latika
authors.initials: L
authors.lastname: Singh
authors.forename: Yuko
authors.initials: Y
authors.lastname: Nakahara
authors.forename: Yukishige
authors.initials: Y
authors.lastname: Ito
authors.forename: Hironobu
authors.initials: H
authors.lastname: Hojo
authors.forename: Yoshiaki
authors.initials: Y
authors.lastname: Nakahara
mesh_terms: D006020:Glycopeptides / Q000138:chemical synthesis* / Q000737:chemistry*; D057927:Hydrophobic and Hydrophilic Interactions; D015394:Molecular Structure; D012694:Serine / Q000737:chemistry*
chemical_list: D006020:Glycopeptides; D012694:Serine