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Monooxygenase Stereoselectivity in the Biosynthesis of Stereoisomeric Spiroacetals in the Cucumber Fly, Bactrocera cucumis

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McErlean, C. S.P., Fletcher, M. T., Wood, B. J., De Voss, J. J. and Kitching, W. (2002) Monooxygenase Stereoselectivity in the Biosynthesis of Stereoisomeric Spiroacetals in the Cucumber Fly, Bactrocera cucumis. Organic Letters, 4 (16). pp. 2775-2778. ISSN 1523-7060

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Article Link: https://doi.org/10.1021/ol0263090

Abstract

The stereoselectivity of hydroxylation of alkyltetrahydropyran-2-ols (or their biological equivalents) in the formation of stereoisomers of 2,8-dimethyl-1,7-dioxaspiro[5.5]undecanes in male Bactrocera cucumis has been investigated. Racemic, (6R)-, and (6S)-6-methyl-2-[5-2H1]-n-pentyltetrahydropyran-2-ol was administered under an [18O2]-enriched atmosphere. The stereochemistry and isotopic composition of generated spiroacetals were monitored by combined enantioselective GC-MS. The monooxygenase(s) strongly prefers the (6S)-substrate and furnishes predominantly the (S)-alcohol and then the (2S,6R,8S)-2,8-dimethyl-1,7-dioxaspiro[5.5]undecane. The (2S,6S,8R) and (2R,6S,8S) (E,Z)-isomers appear to be derived in vivo predominantly from (R)-hydroxylation of the (6S)-tetrahydropyranol.

Item Type:Article
Subjects:Science > Biology > Biochemistry
Live Archive:17 Jan 2024 03:36
Last Modified:17 Jan 2024 03:36

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