Probing replacement of pyrophosphate via click chemistry; synthesis of UDP-sugar analogues as potential glycosyl transferase inhibitors

Kar Kheng Yeoh; Terry D Butters; Brendan Wilkinson; Antony J Fairbanks

doi:10.1016/j.carres.2009.01.001

Probing replacement of pyrophosphate via click chemistry; synthesis of UDP-sugar analogues as potential glycosyl transferase inhibitors

Kar Kheng Yeoh
, Terry D Butters
, Brendan Wilkinson
, Antony J Fairbanks

Chemistry

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

38 Citations (Scopus)

Abstract

A series of potential UDP-sugar mimics were readily synthesised by copper(I) catalysed modified Huisgen cycloaddition of the corresponding a-propargyl glycosides with 5-azido uridine in aqueous solution. None of the compounds accessed displayed significant inhibitory activity at concentrations of up to 4.5 mM in an assay against bovine milk b-1,4-galactosyltransferase.

Original language	English
Pages (from-to)	586-591
Journal	Carbohydrate Research
Volume	344
Issue number	5
DOIs	https://doi.org/10.1016/j.carres.2009.01.001
Publication status	Published - 2009

Keywords

Organic Chemical Synthesis
Biologically Active Molecules
Medicinal and Biomolecular Chemistry

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10.1016/j.carres.2009.01.001

https://hdl.handle.net/1959.11/22984

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title = "Probing replacement of pyrophosphate via click chemistry; synthesis of UDP-sugar analogues as potential glycosyl transferase inhibitors",

abstract = "A series of potential UDP-sugar mimics were readily synthesised by copper(I) catalysed modified Huisgen cycloaddition of the corresponding a-propargyl glycosides with 5-azido uridine in aqueous solution. None of the compounds accessed displayed significant inhibitory activity at concentrations of up to 4.5 mM in an assay against bovine milk b-1,4-galactosyltransferase.",

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journal = "Carbohydrate Research",

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AU - Wilkinson, Brendan

AU - Fairbanks, Antony J

PY - 2009

Y1 - 2009

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AB - A series of potential UDP-sugar mimics were readily synthesised by copper(I) catalysed modified Huisgen cycloaddition of the corresponding a-propargyl glycosides with 5-azido uridine in aqueous solution. None of the compounds accessed displayed significant inhibitory activity at concentrations of up to 4.5 mM in an assay against bovine milk b-1,4-galactosyltransferase.

KW - Organic Chemical Synthesis

KW - Biologically Active Molecules

KW - Medicinal and Biomolecular Chemistry

U2 - 10.1016/j.carres.2009.01.001

DO - 10.1016/j.carres.2009.01.001

M3 - Article

SN - 0008-6215

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JO - Carbohydrate Research

JF - Carbohydrate Research

IS - 5

ER -

Probing replacement of pyrophosphate via click chemistry; synthesis of UDP-sugar analogues as potential glycosyl transferase inhibitors

Abstract

Keywords

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