4675-61-0Relevant articles and documents
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Nunn
, p. 313,314 (1952)
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Phase behavior of a designed cyclopropyl analogue of monoolein: Implications for low-temperature membrane protein crystallization
Salvati Manni, Livia,Zabara, Alexandru,Osornio, Yazmin M.,Sch??ppe, Jendrik,Batyuk, Alexander,Pl??ckthun, Andreas,Siegel, Jay S.,Mezzenga, Raffaele,Landau, Ehud M.
, p. 1027 - 1031 (2015)
Lipidic cubic phases (LCPs) are used in areas ranging from membrane biology to biodevices. Because some membrane proteins are notoriously unstable at room temperature, and available LCPs undergo transformation to lamellar phases at low temperatures, development of stable low-temperature LCPs for biophysical studies of membrane proteins is called for. Monodihydrosterculin (MDS) is a designer lipid based on monoolein (MO) with a configurationally restricted cyclopropyl ring replacing the olefin. Small-angle X-ray scattering (SAXS) analyses revealed a phase diagram for MDS lacking the high-temperature, highly curved reverse hexagonal phase typical for MO, and extending the cubic phase boundary to lower temperature, thereby establishing the relationship between lipid molecular structure and mesophase behavior. The use of MDS as a new material for LCP-based membrane protein crystallization at low temperature was demonstrated by crystallizing bacteriorhodopsin at 20?°C as well as 4?°C.
Synthesis of Cyclopropane Fatty Acids by C(sp3)?C(sp3) Cross-Coupling Reaction and Formal Synthesis of α-Mycolic Acid
Iwasaki, Takanori,Terahigashi, Shohei,Wang, Yufei,Tanaka, Arisa,Zhao, Hanqing,Fujimoto, Yukari,Fukase, Koichi,Kambe, Nobuaki
, p. 3810 - 3817 (2018/09/18)
An iterative Ni-catalyzed C(sp3)?C(sp3) cross-coupling reaction of a novel cis-cyclopropane containing bifunctional building blocks with alkyl halides and alkyl Grignard reagents enabled the introduction of a cyclopropane ring into the desired position(s) of saturated carbon frameworks, providing a straightforward synthetic route to cyclopropane fatty acids. The present method creates a direct route for the construction of saturated carbon frameworks, and can avoid the tedious multistep operations based on unsaturated functional group manipulations that are often employed in conventional synthetic routes. This method could be applicable to the synthesis of trans-cyclopropane fatty acids and enantioenriched cyclopropane fatty acids. Formal synthesis of α-mycolic acid was achieved by the C(sp3)?C(sp3) cross-coupling reaction of cyclopropane-containing bifunctional building blocks. (Figure presented.).
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
