Azido glycoside primer: A versatile building block for the biocombinatorial synthesis of glycosphingolipid analogues

Maria Carmelita Z. Kasuya, Lai X. Wang, Yuan C. Lee, Motoaki Mitsuki, Hideki Nakajima, Yoshiaki Miura, Toshinori Sato, Kenichi Hatanaka, Sadako Yamagata, Tatsuya Yamagata

Research output: Contribution to journalArticle

43 Citations (Scopus)

Abstract

A lactoside primer, 12-azidododecyl β-lactoside, was synthesized via the Koenigs-Knorr method by glycosylation of 1,12-dodecyldiol with perbenzoylated lactosyl bromide. The presence of the 2-O-acyl substituent in the donor gave the β-lactoside, and an excess of acceptor ensured monoglycosylation of the diol. Mesylation of the ω-hydroxyl group in the aglycon, followed by displacement of the mesylate with azide and subsequent O-debenzoylation gave the desired ω-azidododecyl β-lactoside. The azido glycoside primer was examined in mouse B16 melanoma cells for its feasibility as a building block for oligosaccharide biosynthesis. Uptake of the azido glycoside primer by B16 cells resulted in the sialylation of the galactose residue of the primer to give a glycosylated product having the same glycan as in ganglioside GM3. After 24 h incubation of B16 cells with the primers, the amount of sialylated ω-azidododecyl β-lactoside primer was 75% of the amount of sialylated n-dodecyl β-lactoside. However, after 48 h incubation, both primers gave equal amounts of the sialylated products. Interestingly, the remaining azido glycoside primer after 48 h incubation was 5.6-fold greater than that of the alkyl primer, indicating degradation of the alkyl primer to a larger extent than the ω-azido glycoside primer. The facile chemical synthesis and the efficient uptake in cells make the azido glycoside primer a versatile building block for the biocombinatorial synthesis of glycolipid oligosaccharides.

Original languageEnglish
Pages (from-to)755-763
Number of pages9
JournalCarbohydrate Research
Volume329
Issue number4
DOIs
Publication statusPublished - 2000 Dec 1
Externally publishedYes

Keywords

  • Azido glycoside primer
  • Lactosyl ceramide analogue
  • Oligosaccharide library
  • Oligosaccharides, biocombinatorial synthesis
  • Saccharide primer, glycosylation

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

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