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Biosynthesis of Tyvelose

THE PURIFICATION AND PROPERTIES OF CYTIDINE DIPHOSPHATE d-GLUCOSE OXIDOREDUCTASE

From the ¹ From the Department of Biology, Rice University, Houston, Texas 77001

Crude extracts of Salmonella typhi catalyze the conversion of cytidine diphosphate d-glucose to CDP-tyvelose. Two intermediates in this reaction sequence have been identified as CDP-4-keto-6-deoxyglucose and CDP-paratose.

The enzyme catalyzing the conversion of CDP-d-glucose to CDP-4-keto-6-deoxyglucose (CDP-d-glucose oxidoreductase) has been purified approximately 50-fold from these extracts, and its properties have been studied. The product of the reaction, CDP-4-keto-6-deoxy-d-glucose, was characterized by chemical reduction. Mild acid hydrolysis of the reduced nucleotide yielded two 6-deoxyhexoses which were identified as d-fucose (6-deoxygalactose) and 6-deoxy-d-glucose by chromatographic, chemical, and enzymatic methods

CDP-d-glucose oxidoreductase has been shown to require nicotinamide adenine dinucleotide. The enzyme was not activated by NADP⁺. However, the over-all reaction from CDP-d-glucose to CDP-tyvelose has been shown to require NADPH, indicating that this cofactor is involved at a later step in the reaction sequence.

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