[18O]-Oxygen incorporation reveals novel pathways in spiroacetal biosynthesis by Bactrocera cacuminata and B. cucumis

Fletcher, Mary T., Wood, Barry J., Brereton, Ian M., Stok, Jeanette E., De Voss, James J. and Kitching, William (2002) [18O]-Oxygen incorporation reveals novel pathways in spiroacetal biosynthesis by Bactrocera cacuminata and B. cucumis. Journal of the American Chemical Society, 124 26: 7666-7667. doi:10.1021/ja026215l


Author Fletcher, Mary T.
Wood, Barry J.
Brereton, Ian M.
Stok, Jeanette E.
De Voss, James J.
Kitching, William
Title [18O]-Oxygen incorporation reveals novel pathways in spiroacetal biosynthesis by Bactrocera cacuminata and B. cucumis
Journal name Journal of the American Chemical Society   Check publisher's open access policy
ISSN 0002-7863
Publication date 2002-07-03
Sub-type Article (original research)
DOI 10.1021/ja026215l
Volume 124
Issue 26
Start page 7666
End page 7667
Total pages 2
Place of publication Washington, D.C., U.S.A
Publisher American Chemical Society
Collection year 2002
Language eng
Subject C1
250300 Organic Chemistry
780103 Chemical sciences
Abstract The origins of the oxygen atoms in 1,7-dioxaspiro[5.5]undecane (1) and hydroxyspiroacetal (2) from Bactrocera cacuminata, and in 2,8-dimethyl-1,7-dioxaspiro[5.5]undecane (3) and hydroxyspiroacetal (4) from B. cucumis, have been investigated by incorporation studies from both [18O2]-dioxygen and [18O]-water. Combined GC-MS examination and high-field NMR analysis have demonstrated that all oxygen atoms in 1 and 2 from B. cacuminata are dioxygen derived, but in contrast, the spiroacetals 3 and 4 from B. cucumis incorporate one ring oxygen from water and one ring oxygen (and the hydroxyl oxygen in 4) from [18O2]-dioxygen. These results reveal not only the generality of monoxygenase mediation of spiroacetal formation in Bactrocera sp., but also an unexpected complexity in their biosynthesis. A general paradigm accommodating these and other observations is presented.
Keyword Chemistry, Multidisciplinary
Fruit-flies
Sex-pheromone
Fatty-acids
Chemistry
Fly
Secretion
Beetle
Q-Index Code C1

 
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Created: Wed, 15 Aug 2007, 03:24:05 EST