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Reactions of saccharides catalyzed by molybdate ions. 42. Epimerization and the molybdate complexes of the aldoses

V. Bílik and M. Matulová

Institute of Chemistry, Centre for Chemical Research, Slovak Academy of Sciences, CS-842 38 Bratislava

 

Abstract: Epimerization of D-[2,3,4,5,6- 13C]mannose catalyzed by the molybdate ions results in formation of D-[1,3,4,5,6- 13C]glucose. In aqueous solutions of ammonium molybdate D-mannose, D-lyxose, D-glucose, and D-xylose in acyclic forms produce binuclear tetradentate molybdate complexes involv­ing the hydrated carbonyl group as well as hydroxyl groups attached to carbon atoms C-2, C-3, and C-4. In the molybdate complexes D-glucose and D-xylose have an arrangement of the carbon chain close to the zig-zag one, while D-mannose and D-lyxose have sickle arrangement. At the same time D-mannose and D-lyxose produce in greater extent tridentate molybdate complex involving  β-anomeric hydroxyl group and the hydroxyl groups bound to carbon atoms C-2 and C-3 of the pyranoid structure of the aldose.  

Full paper in Portable Document Format: 442a257.pdf

 

Chemical Papers 44 (2) 257–265 (1990)

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