The Metabolism of Cyclopropane Fatty Acids by Tetrahymena pyriformis

Tipton, Charles M.; Al-Shathir, Najah M.

doi:10.1016/s0021-9258(19)43012-3

Cited by 9 publications

(2 citation statements)

References 17 publications

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“…Tipton and Al-Shathir investigated the degradation of cyclopropane fatty acids in whole cells of Tetrahymena pyriformis . From labeling experiments using cis -11,12-[methylene- 14 C]methyleneoctadecanoic acid ( 142 ), they derived the degradation route shown in Scheme , which is supported by the detection of formation of [2- 14 C]acetate ( 143 ).…”

Section: Catabolism Of Cyclopropane Fatty Acidsmentioning

confidence: 96%

Biosynthesis and Metabolism of Cyclopropane Rings in Natural Compounds

2003

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Section: Catabolism Of Cyclopropane Fatty Acidsmentioning

confidence: 96%

Biosynthesis and Metabolism of Cyclopropane Rings in Natural Compounds

2003

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“…Rats apparently cannot metabolize the cyclopropyl ring in acids such as cis-9,-10-methanooctadecanoic acid (Chung, 1966;Wood and Reiser, 1965). Apparently the fungus Fusarium oxysporum can metabolize cyclopropanecarboxylic acid to -hydroxybutyric acid (Schiller and Chung, 1970;Guilbert and Chung, 1974) via the carnitine ester (see also Tipton and Al-Shathir, 1974). In view of the recent work by Guilbert and Chung (1974) on the critical role of 3cyclopropylcarbonyloxycarnitine in F. oxysporum and the work of Buncombe and Rising (1972a) on the effects of cyclopropanecarboxylic acid and its carnitine ester on mitochondrial processes in the rat liver, it is possible that the mite ovicidal effect is related to the disruption of fatty acid metabolism in the mite eggs.…”

Section: Discussionmentioning

confidence: 99%

Ovicidal activity and its relation to chemical structure for the two-spotted spider mite (Tetranychus urticae Koch) in a new class of miticides containing the cyclopropyl group

Ca¹,

We²,

Gb³

et al. 1976

J. Agric. Food Chem.

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Simmons‐Smith Cyclopropanation Reaction

2001

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Almost 30 years after Emschwiller prepared IZnCH 2 I, Simmons and Smith discovered that the reagent formed by mixing a zinc‐copper couple with CH 2 I 2 in ether could be used for the stereospecific conversion of alkenes to cyclopropanes. Nowadays, the Simmons‐Smith cyclopropanation reaction is one of the most widely used reactions in the organic chemist's arsenal for the conversion of olefins into cyclopropanes. This popularity is mainly due to the stereospecificity of the reaction with respect to the double bond geometry and its compatibility with a wide range of functional groups. The chemoselectivity of the reaction toward some olefins is excellent and very few side reactions are observed with functionalized substrates. The metal carbenoid is electrophilic in nature and electron‐rich alkenes usually react much faster than electron‐poor alkenes. Furthermore, the ability to use proximal hydroxy or ether groups to dictate the stereochemical outcome of the CC bond forming process was recognized early on, and this unique property has been successfully exploited on numerous occasions. It has been recognized that halomethylmetal reagents are powerful synthetic tools for the stereoselective addition of a methylene unit to chiral acyclic allylic alcohols and allylic ethers. In addition, the use of halomethylzinc reagents in the presence of chiral additives is one of the few ways to cyclopropanate allylic alcohols efficiently and with good enantiocontrol. Carbenoids can be divided into the following two classes: (1) those of general structure MCH 2 X and (2) those corresponding to M = CH 2 . This chapter is focussed exclusively on the first class in which M = Zn, Sm, or Al. Although other metal carbenoids of type MCH 2 X, such as those derived from Cu, Cd, Hg, and In, have been reported to be effective reagents for the cyclopropanation of some olefins, they have been used only sporadically, and this review does not highlight these reactions. This chapter covers cyclopropanation reactions involving haloalkylzinc, aluminum, and samarium reagents published since the comprehensive chapter in Organic Reactions by Simmons that surveyed the literature up to 1973.

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The Metabolism of Cyclopropane Fatty Acids by Tetrahymena pyriformis

Cited by 9 publications

References 17 publications

Biosynthesis and Metabolism of Cyclopropane Rings in Natural Compounds

Biosynthesis and Metabolism of Cyclopropane Rings in Natural Compounds

Ovicidal activity and its relation to chemical structure for the two-spotted spider mite (Tetranychus urticae Koch) in a new class of miticides containing the cyclopropyl group

Simmons‐Smith Cyclopropanation Reaction

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