title: Glycosylation of Nα-lauryl-O-(β-D-xylopyranosyl)-L-serinamide as a saccharide primer in cells.
abstract: N(α)-Lauryl-O-(β-D-xylopyranosyl)-L-serinamide (Xyl-Ser-C12) was synthesized as a saccharide primer to obtain oligosaccharides of glycosaminoglycan using the glycan biosynthetic potential of mouse osteosarcoma FBJ-S1 cells and Chinese hamster ovary (CHO) cells. The glycosylated products secreted into the culture medium were collected and analyzed by liquid chromatography-mass spectrometry and glycosidase digestion. The structure of the Xyl-Ser-C12 derivatives was investigated. Several glycosaminoglycan-type oligosaccharides, such as GalNAc-(GlcA-GlcNAc)(n)-GlcA-Gal-Gal-Xyl-Ser-C12, were detected, and identified as intermediates of the biosynthesis of heparan sulfate glycosaminoglycans. Xyl-Ser-C12 exhibited greater acceptor activity for the glycosylation of glycosaminoglycan-type oligosaccharides than p-nitrophenyl-β-D-xylopyranoside.
authors.affiliation: Department of Biosciences and Informatics, Keio University, Hiyoshi, Yokohama 223-8522, Japan.
authors.forename: Yinan
authors.initials: Y
authors.lastname: Wang
authors.forename: Tomoaki
authors.initials: T
authors.lastname: Kumazawa
authors.forename: Keisuke
authors.initials: K
authors.lastname: Shiba
authors.forename: Kenji
authors.initials: K
authors.lastname: Osumi
authors.forename: Mamoru
authors.initials: M
authors.lastname: Mizuno
authors.forename: Toshinori
authors.initials: T
authors.lastname: Sato
mesh_terms: D000818:Animals; D016466:CHO Cells; D002470:Cell Survival; D002478:Cells, Cultured; D006224:Cricetinae; D006026:Glycoside Hydrolases / Q000378:metabolism; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D006031:Glycosylation; D055666:Lipopeptides / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D051379:Mice; D008807:Mice, Inbred BALB C; D015394:Molecular Structure; D009844:Oligosaccharides / Q000096:biosynthesis* / Q000737:chemistry / Q000378:metabolism; D012694:Serine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism
chemical_list: D006027:Glycosides; D055666:Lipopeptides; D009844:Oligosaccharides; D012694:Serine; D006026:Glycoside Hydrolases