The composition of 2-keto aldoses in organic solvents as determined by NMR spectroscopy.
The composition of the 2-keto aldoses D-glucosone (1), 6-deoxy-D-glucosone (2), D-allosone (3), and D-galactosone (4) in organic solvents has been determined using NMR spectroscopy. Whereas these keto aldoses form mixtures with up to 15 different isomers in water, the number of forms is significantly decreased in organic solvents. Equilibrium mixtures of 1, 2, and 4 in Me(2)SO, DMF, and pyridine consist to 70-90% of the prevailing alpha-1,5-pyranose form. Two bicyclic forms with a proportion of 80% are the main isomers of 3 in pyridine. Generally, forms with non-hydrated keto functions prevail in non-aqueous solutions.
Freimund
Stefan
S
Carl v. Ossietzky University of Oldenburg, FB Chemistry, P.O. Box 2503, D-26121, Oldenburg, Germany. freimund@tech.chem.ethz.ch
Köpper
Sabine
S
D000447:Aldehydes / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009930:Organic Chemicals / Q000737:chemistry*; D012997:Solvents / Q000737:chemistry*; D013329:Structure-Activity Relationship
D000447:Aldehydes; D009930:Organic Chemicals; D012997:Solvents