Issue 7, 2010
From the journal:

Organic & Biomolecular Chemistry

The UDP-Galpmutase catalyzed isomerization: synthesis and evaluation of 1,4-anhydro-β-d-galactopyranose and its [2.2.2] methylenehomologue†

Ali Sadeghi-Khomami,a   Tatiana J. Forcada,a   Claire Wilson,a   David A. R. Sandersb  and  Neil R. Thomas*a  

* Corresponding authors

a School of Chemistry, Centre for Biomolecular Sciences, University of Nottingham, University Park, Nottingham, United Kingdom
E-mail: neil.thomas@nottingham.ac.uk

b Department of Chemistry, University of Saskatchewan, Saskatoon, Canada

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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Article information

DOI
https://doi.org/10.1039/B917409E
Article type
Paper
Submitted
24 Aug 2009
Accepted
23 Dec 2009
First published
08 Feb 2010

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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