Synthesis of Unsaturated Aminopyranosides as Possible Transition State Mimics for Glycosidases

Allan M. Jordan; Helen M I Osborn; Petra M. Stafford; George Tzortzis; Robert A. Rastall

doi:10.1081/CAR-120026469

Synthesis of Unsaturated Aminopyranosides as Possible Transition State Mimics for Glycosidases

Allan M. Jordan, Helen M I Osborn^*, Petra M. Stafford, George Tzortzis, Robert A. Rastall

^*Corresponding author for this work

The University of Reading

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

Abstract

Four unsaturated aminopyranosides have been prepared as possible transition-state mimics targeted towards carbohydrate processing enzymes. The conformations of the protonated aminosugars have been investigated by molecular modelling and their ability to inhibit α- and β-glucosidases and an α-mannosidase have been probed. Two targets proved moderate inhibitors of α-glucosidases from Brewer's yeast and Bacillus stearothermophilus.

Original language	English
Pages (from-to)	705-717
Number of pages	13
Journal	Journal of Carbohydrate Chemistry
Volume	22
Issue number	7-8
DOIs	https://doi.org/10.1081/CAR-120026469
Publication status	Published - 2003

Keywords

Glycosyl processing enzyme
Inhibitor
Oligosaccharide

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10.1081/CAR-120026469

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abstract = "Four unsaturated aminopyranosides have been prepared as possible transition-state mimics targeted towards carbohydrate processing enzymes. The conformations of the protonated aminosugars have been investigated by molecular modelling and their ability to inhibit α- and β-glucosidases and an α-mannosidase have been probed. Two targets proved moderate inhibitors of α-glucosidases from Brewer's yeast and Bacillus stearothermophilus.",

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AU - Rastall, Robert A.

PY - 2003

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N2 - Four unsaturated aminopyranosides have been prepared as possible transition-state mimics targeted towards carbohydrate processing enzymes. The conformations of the protonated aminosugars have been investigated by molecular modelling and their ability to inhibit α- and β-glucosidases and an α-mannosidase have been probed. Two targets proved moderate inhibitors of α-glucosidases from Brewer's yeast and Bacillus stearothermophilus.

AB - Four unsaturated aminopyranosides have been prepared as possible transition-state mimics targeted towards carbohydrate processing enzymes. The conformations of the protonated aminosugars have been investigated by molecular modelling and their ability to inhibit α- and β-glucosidases and an α-mannosidase have been probed. Two targets proved moderate inhibitors of α-glucosidases from Brewer's yeast and Bacillus stearothermophilus.

KW - Glycosyl processing enzyme

KW - Inhibitor

KW - Oligosaccharide

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ER -

Synthesis of Unsaturated Aminopyranosides as Possible Transition State Mimics for Glycosidases

Abstract

Keywords

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