Synthesis of α-galactosyl ceramide analogues with an α-triazole at the anomeric carbon

Anthony W. McDonagh; Paul V. Murphy

doi:10.13025/14976

Synthesis of α-galactosyl ceramide analogues with an α-triazole at the anomeric carbon

Anthony W. McDonagh
, Paul V. Murphy

Infectious Disease

University of Galway

Research output: Contribution to a Journal (Peer & Non Peer) › Article › peer-review

12 Citations (Scopus)

1 Downloads (Pure)

Abstract

The synthesis of 1,2,3-triazole containing analogues of α-GalCer and galacturonic acid containing Sphingomonous cell wall antigens is described. Anomerisation was used to provide the required α-glycosyl azide precursor. Copper azide-alkyne cycloaddition (CuAAC) generated the α-triazole linkage.

Original language	English
Pages (from-to)	3191-3196
Number of pages	6
Journal	Tetrahedron
Volume	70
Issue number	19
DOIs	https://doi.org/10.13025/14976 https://doi.org/10.1016/j.tet.2014.03.029
Publication status	Published - 13 May 2014

Keywords

Acids
Anomerisation
Bacterial
Chemistry
CuAAC
Cycloaddition
Derivatives
Glycoclusters
Glycolipid
Glycosphingolipids
Glycosyl azide
Infections
Protecting group
Sugars

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10.13025/14976Licence: CC BY
10.1016/j.tet.2014.03.029

Tetrahedron Revision (For ARAN) (1)Accepted author manuscript, 454 KBLicence: CC BY

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title = "Synthesis of α-galactosyl ceramide analogues with an α-triazole at the anomeric carbon",

abstract = "The synthesis of 1,2,3-triazole containing analogues of α-GalCer and galacturonic acid containing Sphingomonous cell wall antigens is described. Anomerisation was used to provide the required α-glycosyl azide precursor. Copper azide-alkyne cycloaddition (CuAAC) generated the α-triazole linkage.",

keywords = "Acids, Anomerisation, Bacterial, Chemistry, CuAAC, Cycloaddition, Derivatives, Glycoclusters, Glycolipid, Glycosphingolipids, Glycosyl azide, Infections, Protecting group, Sugars",

author = "McDonagh, \{Anthony W.\} and Murphy, \{Paul V.\}",

year = "2014",

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day = "13",

doi = "10.13025/14976",

language = "English",

volume = "70",

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T1 - Synthesis of α-galactosyl ceramide analogues with an α-triazole at the anomeric carbon

AU - McDonagh, Anthony W.

AU - Murphy, Paul V.

PY - 2014/5/13

Y1 - 2014/5/13

N2 - The synthesis of 1,2,3-triazole containing analogues of α-GalCer and galacturonic acid containing Sphingomonous cell wall antigens is described. Anomerisation was used to provide the required α-glycosyl azide precursor. Copper azide-alkyne cycloaddition (CuAAC) generated the α-triazole linkage.

AB - The synthesis of 1,2,3-triazole containing analogues of α-GalCer and galacturonic acid containing Sphingomonous cell wall antigens is described. Anomerisation was used to provide the required α-glycosyl azide precursor. Copper azide-alkyne cycloaddition (CuAAC) generated the α-triazole linkage.

KW - Acids

KW - Anomerisation

KW - Bacterial

KW - Chemistry

KW - CuAAC

KW - Cycloaddition

KW - Derivatives

KW - Glycoclusters

KW - Glycolipid

KW - Glycosphingolipids

KW - Glycosyl azide

KW - Infections

KW - Protecting group

KW - Sugars

UR - http://hdl.handle.net/10379/5664

UR - https://www.scopus.com/pages/publications/84898485079

U2 - 10.13025/14976

DO - 10.13025/14976

M3 - Article

SN - 0040-4020

VL - 70

SP - 3191

EP - 3196

JO - Tetrahedron

JF - Tetrahedron

IS - 19

ER -

Synthesis of α-galactosyl ceramide analogues with an α-triazole at the anomeric carbon

Abstract

Keywords

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