title: Glycosylation of dodecyl 2-acetamido-2-deoxy-beta-D-glucopyranoside and dodecyl beta-D-galactopyranosyl-(1-->4)-2-acetamido-2-deoxy-beta-D-glucopyranoside as saccharide primers in cells.
abstract: Syntheses of oligosaccharides expressed on cells are indispensable for the improvement of the functional analyses of the oligosaccharides and their applications. We are developing saccharide primers for synthesizing oligosaccharides using living cells. In this study, dodecyl 2-acetamido-2-deoxy-beta-D-glucopyranoside (GlcNAc-C12) and dodecyl beta-D-galactopyranosyl-(1-->4)-2-acetamido-2-deoxy-beta-D-glucopyranoside (LacNAc-C12) were examined for their abilities to prime the syntheses of neolacto-series oligosaccharides in HL60 cells. When GlcNAc-C12 was incubated with HL60 cells in serum-free medium for 2 days, 14 kinds of glycosylated products were collected from the culture medium. They were separated by high-performance liquid chromatography. The sequences of the products were determined to be neolacto-series oligosaccharides including Lewis(X), sialyl Lewis(X), polylactosamine, and sialylpolylactosamine by mass spectrometry. GlcNAc-C12 was also glycosylated by B16 cells and gave sialyllactosamine. Furthermore, LacNAc-C12 gave similar glycosylated products to GlcNAc-C12.
authors.affiliation: Department of Biosciences and Informatics, Keio University, Yokohama 223-8522, Japan. sato@bio.keio.ac.jp
authors.forename: Toshinori
authors.initials: T
authors.lastname: Sato
authors.forename: Minako
authors.initials: M
authors.lastname: Takashiba
authors.forename: Rumi
authors.initials: R
authors.lastname: Hayashi
authors.forename: Xingyu
authors.initials: X
authors.lastname: Zhu
authors.forename: Tatsuya
authors.initials: T
authors.lastname: Yamagata
mesh_terms: D000117:Acetylglucosamine / Q000031:analogs & derivatives / Q000378:metabolism* / Q000494:pharmacology; D000606:Amino Sugars / Q000737:chemistry; D002240:Carbohydrate Sequence; D049109:Cell Proliferation / Q000187:drug effects; D007851:Dodecanol / Q000737:chemistry; D006031:Glycosylation; D018922:HL-60 Cells; D006801:Humans; D007785:Lactose / Q000031:analogs & derivatives / Q000378:metabolism* / Q000494:pharmacology; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000096:biosynthesis* / Q000737:chemistry / Q000494:pharmacology; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization
chemical_list: D000606:Amino Sugars; D009844:Oligosaccharides; D007851:Dodecanol; C000458:N-acetyllactosamine; D007785:Lactose; D000117:Acetylglucosamine