𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Synthesis and biomethylenation of two homoallylically fluorinated oleic acids

✍ Scribed by Peter H. Buist; Judy M. Findlay; Gabriel Léger; Robert A. Pon

Book ID
104227799
Publisher
Elsevier Science
Year
1987
Tongue
French
Weight
264 KB
Volume
28
Category
Article
ISSN
0040-4039

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✦ Synopsis

Methyl 7-fluorooleate and methyl 12-fluorooleate have been synthesized in racemic form. Both of these compounds are incorporated into L. plantarum but are methylenated to a different extent. The synthesis of fluorinated biomolecules continues to be an important activity both in a theoretical and practical sense.' Fluorinated fatty acids have attracted some attention because of their latent toxicity2 and their use in biophysical studies. 3 In addition, these compounds seem attractive mechanistic probes for the many biological modifications of fatty acid hydrocarbon chains. In particular, we were interested in measuring the effect of fluorine substitution on the incorporation and biomethylenation of olefinic fatty acids by the microorganism, Lactobacillus plantarum (Scheme 1).

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