Glycosylation of Nα-lauryl-O-(β-d-xylopyranosyl)-l- serinamide as a saccharide primer in cells

Yinan Wang, Tomoaki Kumazawa, Keisuke Shiba, Kenji Osumi, Mamoru Mizuno, Toshinori Sato

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5 Citations (Scopus)

Abstract

Nα-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.

Original languageEnglish
Pages (from-to)33-40
Number of pages8
JournalCarbohydrate Research
Volume361
DOIs
Publication statusPublished - 2012 Nov 1

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Keywords

  • FBJ osteosarcoma
  • Glycosaminoglycan
  • Oligosaccharide
  • Saccharide primer

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

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