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Original Articles

Characterization of Enediol-Containing Tautomers of L-Xylosone

, , , &
Pages 1073-1083 | Received 15 Jan 1996, Accepted 30 Jul 1996, Published online: 22 Aug 2006
 

ABSTRACT

Two interconvertible enediol group-containing reductones were produced nonenzymatically from L-xylosone in citrate-phosphate buffer (pH 6.0). These compounds were oxidized by ascorbate oxidase (E.C. 1.10.3.3.) and had ability to reduce 2.6-dichloroindophenol. GLC-MS analysis of trimethylsilylated L-xylosone indicates that it exists in several tautomeric forms including the enediol group-containing reductones which are L-glycero-2-pentenopyranose and L-glycero-2-pentenofuranose. The production rates of both reductones from L-xylosone were proportional to pH within a pH range 4 to 7, and above that pH range further degradation of the reductones occurred.

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