Disaccharides oxidation

J. Walter and H.-J. Jodening, Kinetic model of disaccharide oxidation by Agrobacterium tumefaciens, Biotechnol. Bioeng., 48 (1995) 12-16. 

To complete the synthesis of keto disaccharide 16, the cyclic carbonate must be cleaved and the C-4 hydroxyl group must be oxidized selectively. With respect to the former objective, it is well known that a metal alkoxide (e. g. sodium methoxide) can easily... 

KEY TERMS carboxylic acid alcohol oxidation disaccharide... 

One notices that the data from the oxidation of melezitose by per-iodic acid confirm the pyranose structure of the D-glucose unit in turanose, and therefore also in the case of maltose, in agreement with the original assignments for both of these disaccharides from methylation studies. 

The D-galactosyl residues are the same as in disaccharide 33, and the fact that ribitol is substituted at 0-2 was evident from the methyl-ation analysis. Finally, a nonreducing tetrasaccharide was obtained, containing D-galactose, 2-acetamido-2-deoxy-D-galactose, and ribitol residues in the proportions 2 1 1. From these results, and periodate-oxidation studies, structure 36 was proposed for the neutral hexa-saccharide. 

On deamination, C-substance that had been treated with alkali and phosphatase yielded the disaccharide 2-0-(2-acetamido-2-deoxy-D-galactosyl)-D-ribitol. Periodate oxidation of C-substance had revealed that the ribitol residue is substituted at 0-2 and 0-5. 

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