title: Synthesis of a carbasugar analogue of a putative intermediate in the UDP-galp-mutase catalyzed isomerization.
abstract: [reaction: see text] The synthesis of the carbasugar analogue of 1,4-anhydro-beta-d-galactopyranose, a proposed intermediate in the reaction catalyzed by uridine diphosphate-alpha-d-Galp mutase, in racemic form via Diels-Alder and Barton decarboxylation chemistry is reported. This compound was found not to inhibit the mutase from Mycobacterium tuberculosis, indicating that the enzyme does not possess a 1,4-anhydro-beta-d-galactopyranose binding pocket.
authors.affiliation: School of Chemistry, Centre for Biomolecular Sciences, University of Nottingham, University Park, UK.
authors.forename: Ali
authors.initials: A
authors.lastname: Sadeghi-Khomami
authors.forename: Alexander J
authors.initials: AJ
authors.lastname: Blake
authors.forename: Claire
authors.initials: C
authors.lastname: Wilson
authors.forename: Neil R
authors.initials: NR
authors.lastname: Thomas
mesh_terms: D002384:Catalysis; D005690:Galactose / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D019751:Intramolecular Transferases / Q000737:chemistry*; D007536:Isomerism; D008968:Molecular Conformation; D015394:Molecular Structure
chemical_list: D019751:Intramolecular Transferases; C098051:UDP-galactopyranose mutase; D005690:Galactose