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Issue 16, 2014
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Phosphodiesters serve as potentially tunable aglycones for fluoro sugar inactivators of retaining β-glycosidases

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Abstract

2-Deoxy-2-fluoroglycosides bearing dibenzyl phosphate and phosphonate aglycones were synthesised and tested as covalent inactivators of several retaining α- and β-glycosidases. β-D-Gluco-, -manno- and -galacto-configured benzyl-benzylphosphonate derivatives efficiently inactivated β-gluco-, β-manno- and β-galactosidases, while α-gluco- and α-manno-configured phosphate and phosphonate derivatives served instead as slow substrates.

Graphical abstract: Phosphodiesters serve as potentially tunable aglycones for fluoro sugar inactivators of retaining β-glycosidases

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Publication details

The article was received on 30 Jan 2014, accepted on 28 Feb 2014 and first published on 03 Mar 2014


Article type: Paper
DOI: 10.1039/C4OB00235K
Citation: Org. Biomol. Chem., 2014,12, 2592-2595
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    Phosphodiesters serve as potentially tunable aglycones for fluoro sugar inactivators of retaining β-glycosidases

    B. P. Rempel and S. G. Withers, Org. Biomol. Chem., 2014, 12, 2592
    DOI: 10.1039/C4OB00235K

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