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

The synthesis of 1,4-anhydro-beta-D-galactopyranose (1,5-anhydro-alpha-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.