Synthetic studies on glycosphingolipids from the Protostomia phyla: Syntheses of arthro-series glycosphingolipids

Isao Ohtsuka; Noriyasu Hada; Mutsumi Sugita; Tadahiro Takeda

doi:10.1016/S0008-6215(02)00295-1

Synthetic studies on glycosphingolipids from the Protostomia phyla: Syntheses of arthro-series glycosphingolipids

Isao Ohtsuka, Noriyasu Hada, Mutsumi Sugita, Tadahiro Takeda

School of Pharmacy

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

27 Citations (Scopus)

Abstract

Glycosphingolipids isolated from larvae of the green-bottle fly, Lucilia caesar, have quite unique structures containing GlcNAcβ-(1→3)-Man and GalNAcβ-(1→4)-GlcNAcβ-(1→3)-Man. We have synthesized two glycosphingolipids, β-D-GlcNAcp-(1→3)-β-D-Manp-(1→4)-β-D-Glcp- (1→1)-Cer and β-D-GalNAcp-(1→4)-β-D-GlcNAcp-(1→3)-β-D-Manp- (1→4)-β-D-Glcp-(1→1)-Cer. A key reaction in the synthetic sequence is the application of the intramolecular aglycon delivery (IAD) approach for the synthesis of the β-mannopyranosidic linkages.

Original language	English
Pages (from-to)	2037-2047
Number of pages	11
Journal	Carbohydrate Research
Volume	337
Issue number	21-23
DOIs	https://doi.org/10.1016/S0008-6215(02)00295-1
Publication status	Published - 2002 Nov 19

Keywords

Arthro-series
Chemical synthesis
Glycosphingolipids
Lucilia caesar

ASJC Scopus subject areas

Analytical Chemistry
Biochemistry
Organic Chemistry

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10.1016/S0008-6215(02)00295-1

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title = "Synthetic studies on glycosphingolipids from the Protostomia phyla: Syntheses of arthro-series glycosphingolipids",

abstract = "Glycosphingolipids isolated from larvae of the green-bottle fly, Lucilia caesar, have quite unique structures containing GlcNAcβ-(1→3)-Man and GalNAcβ-(1→4)-GlcNAcβ-(1→3)-Man. We have synthesized two glycosphingolipids, β-D-GlcNAcp-(1→3)-β-D-Manp-(1→4)-β-D-Glcp- (1→1)-Cer and β-D-GalNAcp-(1→4)-β-D-GlcNAcp-(1→3)-β-D-Manp- (1→4)-β-D-Glcp-(1→1)-Cer. A key reaction in the synthetic sequence is the application of the intramolecular aglycon delivery (IAD) approach for the synthesis of the β-mannopyranosidic linkages.",

keywords = "Arthro-series, Chemical synthesis, Glycosphingolipids, Lucilia caesar",

author = "Isao Ohtsuka and Noriyasu Hada and Mutsumi Sugita and Tadahiro Takeda",

note = "Funding Information: This work was supported by a Grant-in-Aid for Scientific Research (No. 12672062) from the Ministry of Education, Science, Sports and Culture of Japan. We gratefully acknowledge financial support in the form of a Sasagawa Scientific Research Grant. The authors are grateful to Ms. J. Hada for providing NMR and MS data.",

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AU - Ohtsuka, Isao

AU - Hada, Noriyasu

AU - Sugita, Mutsumi

AU - Takeda, Tadahiro

N1 - Funding Information: This work was supported by a Grant-in-Aid for Scientific Research (No. 12672062) from the Ministry of Education, Science, Sports and Culture of Japan. We gratefully acknowledge financial support in the form of a Sasagawa Scientific Research Grant. The authors are grateful to Ms. J. Hada for providing NMR and MS data.

PY - 2002/11/19

Y1 - 2002/11/19

N2 - Glycosphingolipids isolated from larvae of the green-bottle fly, Lucilia caesar, have quite unique structures containing GlcNAcβ-(1→3)-Man and GalNAcβ-(1→4)-GlcNAcβ-(1→3)-Man. We have synthesized two glycosphingolipids, β-D-GlcNAcp-(1→3)-β-D-Manp-(1→4)-β-D-Glcp- (1→1)-Cer and β-D-GalNAcp-(1→4)-β-D-GlcNAcp-(1→3)-β-D-Manp- (1→4)-β-D-Glcp-(1→1)-Cer. A key reaction in the synthetic sequence is the application of the intramolecular aglycon delivery (IAD) approach for the synthesis of the β-mannopyranosidic linkages.

AB - Glycosphingolipids isolated from larvae of the green-bottle fly, Lucilia caesar, have quite unique structures containing GlcNAcβ-(1→3)-Man and GalNAcβ-(1→4)-GlcNAcβ-(1→3)-Man. We have synthesized two glycosphingolipids, β-D-GlcNAcp-(1→3)-β-D-Manp-(1→4)-β-D-Glcp- (1→1)-Cer and β-D-GalNAcp-(1→4)-β-D-GlcNAcp-(1→3)-β-D-Manp- (1→4)-β-D-Glcp-(1→1)-Cer. A key reaction in the synthetic sequence is the application of the intramolecular aglycon delivery (IAD) approach for the synthesis of the β-mannopyranosidic linkages.

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Synthetic studies on glycosphingolipids from the Protostomia phyla: Syntheses of arthro-series glycosphingolipids

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Keywords

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