Synthesis of a carbasugar analogue of a putative intermediate in the UDP-galp-mutase catalyzed isomerization.
[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.
Sadeghi-Khomami
Ali
A
School of Chemistry, Centre for Biomolecular Sciences, University of Nottingham, University Park, UK.
Blake
Alexander J
AJ
Wilson
Claire
C
Thomas
Neil R
NR
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
D019751:Intramolecular Transferases; C098051:UDP-galactopyranose mutase; D005690:Galactose