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A divergent synthesis of 2-acyl derivatives of PUGNAc yields selective inhibitors of O-GlcNAcase

A divergent synthesis of 2-acyl derivatives of PUGNAc yields selective inhibitors of O-GlcNAcase A divergent route facilitating the rapid synthesis of a series of -(2-acetamido-2-deoxy--glucopyranosylidene)amino -phenylcarbamate (PUGNAc)-based inhibitors, bearing different -acyl groups has been developed. All compounds of this series are inhibitors of both human -GlcNAcase and human β-hexosaminidase, yet some effectively exploit differences between the active site architectures of these two human enzymes which render them selective for -GlcNAcase. Such inhibitors may be valuable tools in dissecting the role of the -GlcNAc post-translational modification at the cellular and organismal level since these compounds may have different pharmacokinetic properties when compared to other inhibitors of β--acetyl-glucosaminidases. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Organic & Biomolecular Chemistry Royal Society of Chemistry

A divergent synthesis of 2-acyl derivatives of PUGNAc yields selective inhibitors of O-GlcNAcase

Stubbs, Keith A.; Zhang, Nelson; Vocadlo, David J.
Royal Society of Chemistry — Feb 21, 2006
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Abstract

A divergent route facilitating the rapid synthesis of a series of -(2-acetamido-2-deoxy--glucopyranosylidene)amino -phenylcarbamate (PUGNAc)-based inhibitors, bearing different -acyl groups has been developed. All compounds of this series are inhibitors of both human -GlcNAcase and human β-hexosaminidase, yet some effectively exploit differences between the active site architectures of these two human enzymes which render them selective for -GlcNAcase. Such inhibitors may be valuable tools in dissecting the role of the -GlcNAc post-translational modification at the cellular and organismal level since these compounds may have different pharmacokinetic properties when compared to other inhibitors of β--acetyl-glucosaminidases.

Journal

Organic & Biomolecular Chemistry – Royal Society of Chemistry

Published: Feb 21, 2006

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