5711-28-4Relevant academic research and scientific papers
Total Synthesis of Cardiolipins Containing Chiral Cyclopropane Fatty Acids
Inuki, Shinsuke,Ohta, Ippei,Ishibashi, Shunichi,Takamatsu, Masayuki,Fukase, Koichi,Fujimoto, Yukari
, p. 7832 - 7838 (2017/08/14)
Cardiolipin (CL) is a phospholipid located in both the eukaryotic mitochondrial inner membrane and the bacterial cell membrane. Some bacterial CLs are known to contain cyclopropane moieties in their acyl chains. Although the CLs are thought to be involved in the innate immune response, there have been few attempts at chemical synthesis of the CLs, and detailed studies of their biological activities are scarce. Thus, we have developed a synthetic route to CLs containing chiral cyclopropane moieties.
Total syntheses of cis-cyclopropane fatty acids: Dihydromalvalic acid, dihydrosterculic acid, lactobacillic acid, and 9,10-methylenehexadecanoic acid
Shah, Sayali,White, Jonathan M.,Williams, Spencer J.
, p. 9427 - 9438 (2014/12/11)
cis-Cyclopropane fatty acids (cis-CFAs) are widespread constituents of the seed oils of subtropical plants, membrane components of bacteria and protozoa, and the fats and phospholipids of animals. We describe a systematic approach to the synthesis of enan
An Unexpected Reversal of Fluorine Substituent Effects in the Biomethylenation of Two Positional Isomers: A Serendipitous Discovery
Buist, Peter H.,Pon, Robert A.
, p. 6240 - 6241 (2007/10/02)
The mechanism of biological cyclopropyl fatty acid biosynthesis as it occurs in Lactobacillus plantarum has been probed using fluorine substituent effects.It has been shown that the pattern of rate retardations induced by homoallylic fluorine substitution is numerically the same but opposite in sense for two series of olefinic fatty acid substrates bearing the double bond at either the 9- or the 11-position.
SYNTHESIS AND BIOMETHYLENATION OF TWO HOMOALLYLICALLY FLUORINATED OLEIC ACIDS
Buist, Peter H.,Findlay, Judy M.,Leger, Gabriel,Pon, Robert A.
, p. 3891 - 3894 (2007/10/02)
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.
