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Journal of Chemical Ecology

Journal of Chemical Ecology

IF: 2.2
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Biosynthesis of tiglic, ethacrylic, and 2-methylbutyric acids in a carabid beetle, Pterostichus (Hypherpes) californicus.

Published:1 May 2007 DOI: 10.1007/s10886-007-9276-3 PMID: 17404818
Athula B Attygalle, Xiaogang Wu, Kipling W Will

Abstract

Tiglic, 2-methylbutyric, and ethacrylic acids are found in the pygidial gland defensive fluid of many carabid beetles. By injecting a deuterium-labeled precursor into the carabid beetle Pterostichus (Hypherpes) californicus, and analyzing the defensive fluid by gas chromatography/mass spectrometry, we were able to demonstrate that tiglic and ethacrylic acids are biosynthesized from isoleucine via 2-methylbutyric acid. Moreover, we observed that the injection of L-isoleucine induces an increased production of tiglic acid in P. californicus. A strong primary kinetic isotope effect was found to operate in the dehydrogenation step of 2-methylbutyric acid to tiglic and ethacrylic acids. Consequently, ethacrylic acid was found to preferentially accumulate the deuterium labeling from [2,3,4,4-(2)H(4)]isoleucine during our biosynthetic experiments.

Substances (5)

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Procduct Name CAS Molecular Formula Supplier Price
2-Methyl butyric acid 116-53-0 C5H10O2 494 suppliers $10.00-$30148.60
Tiglic acid 80-59-1 C5H8O2 347 suppliers $5.00-$2483.25
Methylbutyric acid 600-07-7 C5H10O2 86 suppliers $31.00-$254.00
2-ETHYLACRYLIC ACID 98 3586-58-1 C5H8O2 33 suppliers $122.00-$1168.20
Isoleucine 7004-09-3 C6H13NO2 18 suppliers Inquiry

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