4675-61-0Relevant academic research and scientific papers
A quantitative assessment of the influence of permanent kinks on the mixing behavior of phospholipids in cholesterol-rich bilayers
Jing, Bingwen,Tokutake, Nobuya,McCullough III, Donald H.,Regen, Steven L.
, p. 15344 - 15345 (2004)
The mixing behavior of a phospholipid containing a cis-cyclopropyl moiety (1) with one that contains two myristoyl groups (3a) has been investigated in fluid bilayers via the nearest-neighbor recognition (NNR) method. In the absence of cholesterol, these lipids mix ideally. In the presence of cholesterol, they show a modest preference for homo-phospholipid association. A trans-form of 1 (i.e., 2) was found to have similar behavior, except that the influence of cholesterol in promoting homo-phospholipid association was greater. Similar results have been found in membranes in which 3a is replaced with a phospholipid bearing two palmitoyol chains (3b). In this case, the effect of the kink is approximately twice as great. The implications of these findings, with respect to the trans-fatty acid debate , are briefly discussed Copyright
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.
NOVEL LYSOPHOSPHATIDIC ACID DERIVATIVE
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Paragraph 0496-0498, (2021/05/28)
PROBLEM TO BE SOLVED: To provide a compound that specifically activates an LPA4 receptor, and a pharmaceutical composition containing the same. SOLUTION: This invention relates to a novel lysophosphatidic acid derivative that has an agonistic action on an LPA4 receptor and is useful for the prevention and/or treatment of a disease with angiodysplasia caused by the LPA4 receptor, or a disease associated with angiopathy, or symptoms associated therewith. This invention also relates to a pharmaceutical composition containing the lysophosphatidic acid derivative. SELECTED DRAWING: None COPYRIGHT: (C)2021,JPOandINPIT
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 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
The newly synthesized linoleic acid derivative FR236924 induces a long-lasting facilitation of hippocampal neurotransmission by targeting nicotinic acetylcholine receptors
Tanaka, Akito,Nishizaki, Tomoyuki
, p. 1037 - 1040 (2007/10/03)
The newly synthesized linoleic acid derivative, FR236924, induces a long-lasting facilitation of hippocampal neurotransmission based on a persistent enhancement in the activity of presynaptic nicotinic ACh receptors via a PKC pathway and the ensuing increase in glutamate release, not only in vitro but in vivo at a low dosage (2 mg/kg, ip), which suggested the possibility of its use as a promising anti-dementia drug.
New family of cyclopropanating reagents: Synthesis, reactivity, and stability studies of iodomethylzinc phenoxides
Charette, Andre B.,Francoeur, Sebastien,Martel, Jonathan,Wilb, Nicole
, p. 4539 - 4542 (2007/10/03)
A valuable alternative to the traditional Simmons-Smith reagents is offered by the title compounds, as a result of their ease of preparation and high reactivities towards unfunctionalized olefins (see scheme).
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.
