Synthesis of neutral glycosphingolipids from Zygomycetes

Noriyasu Hada, Junko Oka, Kyoko Hakamata, Kenji Yamamoto, Tadahiro Takeda

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

Novel neutral glycosphingolipids (NGSLs) containing Gal-α1→6Gal, previously found in the Zygomycetes species Mucor hiemalis, were synthesized. The structures of these compounds are different from those of other fungal GSLs, and they are expected to be involved in host-parasite interactions. A key step in their synthesis is direct 1,2-cis α-selective galactosylation of 4,6-diol tri- and tetrasaccharide acceptors with a galactosyl donor in the presence of N-iodosuccinimide (NIS)/trifluoromethanesulfonic acid (TfOH). The fully protected glycosides were deprotected to give the two target glycosphingolipids.

Original languageEnglish
Pages (from-to)2315-2324
Number of pages10
JournalCarbohydrate Research
Volume343
Issue number13
DOIs
Publication statusPublished - 2008 Sep 8

Fingerprint

Neutral Glycosphingolipids
Mucor
Trisaccharides
Host-Parasite Interactions
Glycosphingolipids
Glycosides
N-iodosuccinimide
trifluoromethanesulfonic acid
Parasites

Keywords

  • α-Galactosylation
  • 1,2-cis-Glycoside
  • Di-tert-butylsilylene group
  • Mucor hiemalis
  • Zygomycetes species

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Organic Chemistry

Cite this

Hada, N., Oka, J., Hakamata, K., Yamamoto, K., & Takeda, T. (2008). Synthesis of neutral glycosphingolipids from Zygomycetes. Carbohydrate Research, 343(13), 2315-2324. https://doi.org/10.1016/j.carres.2008.04.019

Synthesis of neutral glycosphingolipids from Zygomycetes. / Hada, Noriyasu; Oka, Junko; Hakamata, Kyoko; Yamamoto, Kenji; Takeda, Tadahiro.

In: Carbohydrate Research, Vol. 343, No. 13, 08.09.2008, p. 2315-2324.

Research output: Contribution to journalArticle

Hada, N, Oka, J, Hakamata, K, Yamamoto, K & Takeda, T 2008, 'Synthesis of neutral glycosphingolipids from Zygomycetes', Carbohydrate Research, vol. 343, no. 13, pp. 2315-2324. https://doi.org/10.1016/j.carres.2008.04.019
Hada N, Oka J, Hakamata K, Yamamoto K, Takeda T. Synthesis of neutral glycosphingolipids from Zygomycetes. Carbohydrate Research. 2008 Sep 8;343(13):2315-2324. https://doi.org/10.1016/j.carres.2008.04.019
Hada, Noriyasu ; Oka, Junko ; Hakamata, Kyoko ; Yamamoto, Kenji ; Takeda, Tadahiro. / Synthesis of neutral glycosphingolipids from Zygomycetes. In: Carbohydrate Research. 2008 ; Vol. 343, No. 13. pp. 2315-2324.
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