Glycosylation of dodecyl 2-acetamido-2-deoxy-β-d-glucopyranoside and dodecyl β-d-galactopyranosyl-(1→4)-2-acetamido-2-deoxy-β-d-glucopyranoside as saccharide primers in cells

Toshinori Sato, Minako Takashiba, Rumi Hayashi, Xingyu Zhu, Tatsuya Yamagata

Research output: Contribution to journalArticlepeer-review

13 Citations (Scopus)

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-β-d-glucopyranoside (GlcNAc-C12) and dodecyl β-d-galactopyranosyl-(1→4)-2-acetamido-2-deoxy-β-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 LewisX, sialyl LewisX, 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.

Original languageEnglish
Pages (from-to)831-838
Number of pages8
JournalCarbohydrate Research
Volume343
Issue number5
DOIs
Publication statusPublished - 2008 Apr 7

Keywords

  • Animal cells
  • Glycosylation
  • N-Acetylglucosamine
  • N-Acetyllactosamine
  • Oligosaccharide
  • Saccharide primer

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

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