Synthesis of neutral glycosphingolipids from Zygomycetes

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

doi:10.1016/j.carres.2008.04.019

Synthesis of neutral glycosphingolipids from Zygomycetes

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

Research output: Contribution to journal › Article › peer-review

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 language	English
Pages (from-to)	2315-2324
Number of pages	10
Journal	Carbohydrate Research
Volume	343
Issue number	13
DOIs	https://doi.org/10.1016/j.carres.2008.04.019
Publication status	Published - 2008 Sept 8
Externally published	Yes

Keywords

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

ASJC Scopus subject areas

Analytical Chemistry
Biochemistry
Organic Chemistry

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10.1016/j.carres.2008.04.019

Cite this

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title = "Synthesis of neutral glycosphingolipids from Zygomycetes",

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.",

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

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T1 - Synthesis of neutral glycosphingolipids from Zygomycetes

AU - Hada, Noriyasu

AU - Oka, Junko

AU - Hakamata, Kyoko

AU - Yamamoto, Kenji

AU - Takeda, Tadahiro

PY - 2008/9/8

Y1 - 2008/9/8

N2 - 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.

AB - 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.

KW - 1,2-cis-Glycoside

KW - Di-tert-butylsilylene group

KW - Mucor hiemalis

KW - Zygomycetes species

KW - α-Galactosylation

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DO - 10.1016/j.carres.2008.04.019

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SN - 0008-6215

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EP - 2324

JO - Carbohydrate Research

JF - Carbohydrate Research

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ER -

Synthesis of neutral glycosphingolipids from Zygomycetes

Abstract

Keywords

ASJC Scopus subject areas

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