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

Research output: Contribution to journalArticle

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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Glycosylation
Glycosaminoglycans
Oligosaccharides
Heparitin Sulfate
Glycoside Hydrolases
Biosynthesis
Liquid chromatography
Osteosarcoma
Cricetulus
Liquid Chromatography
Mass spectrometry
Polysaccharides
Culture Media
Digestion
Ovary
Mass Spectrometry
Cells
Derivatives
serinamide

Keywords

  • FBJ osteosarcoma
  • Glycosaminoglycan
  • Oligosaccharide
  • Saccharide primer

ASJC Scopus subject areas

  • Biochemistry
  • Analytical Chemistry
  • Organic Chemistry

Cite this

Glycosylation of Nα-lauryl-O-(β-d-xylopyranosyl)-l- serinamide as a saccharide primer in cells. / Wang, Yinan; Kumazawa, Tomoaki; Shiba, Keisuke; Osumi, Kenji; Mizuno, Mamoru; Sato, Toshinori.

In: Carbohydrate Research, Vol. 361, 01.11.2012, p. 33-40.

Research output: Contribution to journalArticle

Wang, Yinan ; Kumazawa, Tomoaki ; Shiba, Keisuke ; Osumi, Kenji ; Mizuno, Mamoru ; Sato, Toshinori. / Glycosylation of Nα-lauryl-O-(β-d-xylopyranosyl)-l- serinamide as a saccharide primer in cells. In: Carbohydrate Research. 2012 ; Vol. 361. pp. 33-40.
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AU - Sato, Toshinori

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