RRC ID 43266
Author Sato T, Takashiba M, Hayashi R, Zhu X, Yamagata T.
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.
Journal Carbohydr Res
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.
Volume 343(5)
Pages 831-8
Published 2008-4-7
DOI 10.1016/j.carres.2008.01.022
PII S0008-6215(08)00040-2
PMID 18262174
MeSH Acetylglucosamine / analogs & derivatives Acetylglucosamine / metabolism* Acetylglucosamine / pharmacology Amino Sugars / chemistry Carbohydrate Sequence Cell Proliferation / drug effects Dodecanol / chemistry Glycosylation HL-60 Cells Humans Lactose / analogs & derivatives Lactose / metabolism* Lactose / pharmacology Molecular Sequence Data Oligosaccharides / biosynthesis* Oligosaccharides / chemistry Oligosaccharides / pharmacology Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization
IF 1.841
Times Cited 12
WOS Category CHEMISTRY, APPLIED CHEMISTRY, ORGANIC BIOCHEMISTRY & MOLECULAR BIOLOGY
Resource
Human and Animal Cells