An efficient and novel method for the synthesis of cardiolipin and its analogs

Lin, Zhen Yang; Ahmad, M. S.; Ali, Shoukath M.; Ahmad, Imran

doi:10.1007/s11745-004-1231-5

Cited by 10 publications

(3 citation statements)

References 22 publications

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“…Chemical Synthesis of T22:6 CL. Chemical synthesis of T22:6 CL was achieved through modification of a published approach (27). Briefly, O-chlorophenyl-and tetrahydropyranyl-protected T22:6 CL was prepared in a single reaction via phosphorylation of di22:6 glycerol in the presence of 2-O-tetrahydropyranylpropanol and subsequently phosphorylated using the bifunctional phosphorylating reagent, O-chlorophenyl dichlorophosphate.…”

Section: Methodsmentioning

confidence: 99%

Shotgun Lipidomics Reveals the Temporally Dependent, Highly Diversified Cardiolipin Profile in the Mammalian Brain: Temporally Coordinated Postnatal Diversification of Cardiolipin Molecular Species with Neuronal Remodeling

et al. 2008

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Large-scale neuronal remodeling through apoptosis occurs shortly after birth in all known mammalian species. Apoptosis, in large part, depends upon critical interactions between mitochondrial membranes and cytochrome c. Herein, we examined the hypothesis that the largescale reorganization of neuronal circuitry after birth is accompanied by profound alterations in cardiolipin (CL) content and molecular species distribution. During embryonic development, over 100 CL molecular species were identified and quantitated in murine neuronal tissues. The embryonic CL profile was notable for the presence of abundant amounts of relatively short aliphatic chains (e.g., palmitoleic and oleic acids). In sharp contrast, after birth, the CL profile contained a remarkably complex repertoire of CL molecular species, in which the signaling fatty acids (i.e., arachidonic and docosahexaenoic acids) were markedly increased. These results identify the rapid remodeling of CL in the perinatal period with resultant alterations in the physical properties of the mitochondrial membrane. The complex distribution of aliphatic chains in the neuronal CL pool is separate and distinct from that in other organs (e.g., heart, liver, etc.), where CL molecular species contain predominantly only one major type of aliphatic chain (e.g., linoleic acid). Analyses of mRNA levels by real-time quantitative polymerase chain reactions suggested that the alterations in CL content were due to the combined effects of both attenuation of de novo CL biosynthesis and decreased remodeling of CL. Collectively, these results provide a new perspective on the complexity of CL in neuronal signaling, mitochondrial bioenergetics, and apoptosis.Cardiolipin (1,3-diphosphatidyl-sn-glycerol, CL) 1 is exclusively present in the mitochondrial membrane of eukaryotic cells (1), whose evolutionary origins can be traced back to bacterial membranes. Each CL molecular species is uniquely comprised of a dimer of two phosphatidyl † This work was supported by NIA Grants R01 AG23168 and R01 AG31675, NIH Grant P01 HL57278, and the Neurosciences Education and Research Foundation.* To whom correspondence should be addressed: Division of Bioorganic Chemistry and Molecular Pharmacology, Department of Internal Medicine, Washington University School of Medicine, Box 8020, 660 South Euclid Avenue, St. Louis, MO 63110. Telephone: (314) 362−2690. Fax: (314) 362−1402. E-mail: xianlin@wustl.edu.. Publisher's Disclaimer: This PDF receipt will only be used as the basis for generating PubMed Central (PMC) documents. PMC documents will be made available for review after conversion (approx. 2−3 weeks time). Any corrections that need to be made will be done at that time. No materials will be released to PMC without the approval of an author. Only the PMC documents will appear on PubMed Central --this PDF Receipt will not appear on PubMed Central. 1 Abbreviation: CL, cardiolipin; FA, fatty acid or fatty acyl; FACO, fatty acyl-CoA oxidase; GAPDH, glyceraldehyde-3-phosphate dehydrogenase; HPLC, high-pe...

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Section: Methodsmentioning

confidence: 99%

Shotgun Lipidomics Reveals the Temporally Dependent, Highly Diversified Cardiolipin Profile in the Mammalian Brain: Temporally Coordinated Postnatal Diversification of Cardiolipin Molecular Species with Neuronal Remodeling

et al. 2008

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“…Other synthetic approaches describe the use of phosphorylating agents such as cyclic enediol pyrophosphates [6][7][8], silver salts of PA [9,10], phosphorus oxychloride [11], and 2-chlorophenyl phosphorodi-(1,2,4-trizolide) [12]. As part of our ongoing research towards the synthesis of cardiolipin and its analogues, we have developed and reported convenient alternative methodologies [13][14][15] based on phosphoramidite chemistry [16,17]. However, all these methods utilize 2-O-protected glycerols along with the phosphorylation or condensation reagents.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 1,3‐ and 1,2‐Diphosphatidylglycerol

Ahmad

Krishna

Ali

et al. 2007

Lipids

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A novel phosphonium salt methodology was utilized for the first time to synthesize 1,3-, and 1,2-diphosphatidylglycerol. Optically active 1,2-di-O-acyl-sn-glyceryl phosphate was coupled with unprotected glycerol in the presence of pyridiniumbromide perbromide and triethylamine to yield, after final removal of phosphate protecting group, the title compounds. The 1,2-diphosphatidylglycerol (1,2-isomer of cardiolipin) may be a member of a new class of phospholipids for industrial applications similar to other phosphocholines.

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“…However, the use of phosphate triesters in preparing phospholipids such as CL having varying FA chain lengths is not well established. As part of our ongoing research toward the synthesis of CL and its analogs (28,29), we have developed a concise and convenient alternate synthetic methodology for CL synthesis based on phosphite chemistry. Herein we report the versatility of this method as exemplified by the synthesis of saturated (lauroyl) CL (Scheme 3) and unsaturated (oleoyl) CL (Scheme 4) as well as ether analogs having FA chains ranging from C 6 to C 18 .…”

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confidence: 99%

A short, concise route to diphosphatidylglycerol (Cardiolipin) and its variants

Krishna¹,

Ahmad²,

Ali³

et al. 2004

Lipids

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A new approach is described for the synthesis of the cardiolipin family of phospholipids that uses phosphonium salt methodology. The method involves the reaction of 2-O-protected glycerol with a trialkyl phosphite derived from 1,2-diacylsn-glycerol in the presence of pyridinium bromide perbromide and triethylamine to afford the phosphoric triesters. The synthesis involves three steps and allows the preparation of a wide range of cardiolipins with different substitution patterns and chain lengths, including unsaturated derivatives. The use of inexpensive protecting groups and the ease of purification facilitate this synthetic route and allow its scale-up in a higher overall yield (72%) than the literature methods.

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An efficient and novel method for the synthesis of cardiolipin and its analogs

Cited by 10 publications

References 22 publications

Shotgun Lipidomics Reveals the Temporally Dependent, Highly Diversified Cardiolipin Profile in the Mammalian Brain: Temporally Coordinated Postnatal Diversification of Cardiolipin Molecular Species with Neuronal Remodeling

Shotgun Lipidomics Reveals the Temporally Dependent, Highly Diversified Cardiolipin Profile in the Mammalian Brain: Temporally Coordinated Postnatal Diversification of Cardiolipin Molecular Species with Neuronal Remodeling

Synthesis of 1,3‐ and 1,2‐Diphosphatidylglycerol

A short, concise route to diphosphatidylglycerol (Cardiolipin) and its variants

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