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Issue 7, 2010
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The UDP-Galp mutase catalyzed isomerization: synthesis and evaluation of 1,4-anhydro-β-D-galactopyranose and its [2.2.2] methylene homologue

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Abstract

The synthesis of 1,4-anhydro-β-D-galactopyranose (1,5-anhydro-α-D-galactofuranose), a proposed intermediate in the ring contraction isomerisation catalyzed by UDP-galactopyranose mutase, together with its [2.2.2] bicyclic methylene homologue, synthesised as a possible competitive inhibitor or alternative substrate, are reported. Neither compound was found to be an inhibitor or substrate for UDP-galactopyranose mutase from Klebsiella pneumoniae.

Graphical abstract: The UDP-Galp mutase catalyzed isomerization: synthesis and evaluation of 1,4-anhydro-β-d-galactopyranose and its [2.2.2] methylene homologue

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Publication details

The article was received on 24 Aug 2009, accepted on 23 Dec 2009 and first published on 08 Feb 2010


Article type: Paper
DOI: 10.1039/B917409E
Org. Biomol. Chem., 2010,8, 1596-1602

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    The UDP-Galp mutase catalyzed isomerization: synthesis and evaluation of 1,4-anhydro-β-D-galactopyranose and its [2.2.2] methylene homologue

    A. Sadeghi-Khomami, T. J. Forcada, C. Wilson, D. A. R. Sanders and N. R. Thomas, Org. Biomol. Chem., 2010, 8, 1596
    DOI: 10.1039/B917409E

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