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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
 
 
 
 
 

Synthesis of the glucuronic acid conjugate of methylazoxymethanol.

The glucuronic acid conjugate of methylazoxymethanol was synthesized by oxidizing the primary alcohol of the glucose moiety of cycasin (methylazoxymethanol-beta-D-glycopyranoside) to a carboxylic acid. The oxidation was carried out by bubbling oxygen gas through a cycasin solution in the presence of a platinum-on-carbon catalyst. A band at 1715 cm-1, not present in the cycasin infrared spectrum, appeared in the spectrum of the oxidized cycasin product, establishing the presence of a carboxylic acid group. The oxidation product is methylazoxymethanol-beta-D-glucosiduronic acid because, when hydrolyzed with Escherichia coli beta-glucuronidase, it produced methylazoxymethanol and glucuronic acid and also indicated retention of the beta-linkage of cycasin. Varying quantities of the synthesized methylazoxymethanol-glucosiduronic acid, injected into Wistar rats of both sexes and of varying weights, were not acutely toxic. The compound was mutagenic to Salmonella typhimurium when preincubated with E. coli beta-glucuronidase, but not when preincubated with bovine liver glucuronidase.[1]

References

  1. Synthesis of the glucuronic acid conjugate of methylazoxymethanol. Matsumoto, H., Takata, R.H., Komeiji, D.Y. Cancer Res. (1979) [Pubmed]
 
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