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Closed Access item Enzymatic desaturation of fatty acids: delta11 desaturase activity on cyclopropane acid probes

Authors:Villorbina, Gemma
Roura, Lidia
Camps Díez, Francisco
Joglar Tamargo, Jesús
Fabriàs, Gemma
Keywords:Cyclopropane fatty acids, Enzymatic desaturation, Spodoptera littoralis, Gas chromatography-mass spectrometry (GC-MS)
Issue Date:6-Mar-2003
Publisher:American Chemical Society
Citation:Journal of Organic Chemistry 68(7): 2820-2829 (2003)
Abstract:The formation of methylenecyclopropanes by enzymatic desaturation of 11-cyclopropylundecanoic acid (1) and its disubstituted derivatives cis- and trans-3−5 has been investigated using the Δ11 desaturase of Spodoptera littoralis as model enzyme. Gas chromatography coupled to mass spectrometry analyses of methanolyzed lipidic extracts from tissues incubated with each probe revealed that all the cyclopropyl fatty acids were transformed into the corresponding 11-cyclopropylidene acids, except for compound trans-5 (5b), which was not desaturated at C11. The formation of methylenecyclopropane 9 as the only reaction product from 1 indicates that a potential radical intermediate is too short-lived to allow rearrangement reactions. Information on the Δ11 desaturase substrate binding domain is provided considering the cyclopropyl probes 3−5 as conformationally restricted analogues of the straight-chain substrates.
Description:10 pages, 6 figures, 3 schemes.-- PMID: 12662058 [PubMed].-- Printed version published Apr 4, 2003.
Publisher version (URL):http://dx.doi.org/10.1021/jo0267100
ISSN:0022-3263 (Print)
1520-6904 (Online)
Appears in Collections:(IQAC) Artículos

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