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Abstract: (Chemical Abstract 2006, : )
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The conformational space of D and L, deoxy and non-deoxy, 5-thio-pyranoses with biological properties as enzymatic inhibitors, was explored using MM and B3LYP/6-31+G* methods, in gas-phase and solution. The preferred ring conformation, for α and β-anomers of 5-thio-L-fucopyranose, was the 1C4 form (about 99%), and for 5-thio-D-glucopyranose and 5-thio-D-mannopyranose, the 4C1 one. The experimental conformational order (4C1 > 1C4 > 2SS) for L-ido derivatives was reproduced only considering the solvent, though for 3-O-methyl-5-thio-α-L-idopyranose, the inclusion of methyl in C3 changed the 2SS form to B1,4 one.
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