Enzyme-mediated synthesis of two diastereoisomeric forms of phosphatidylglycerol and of diphosphatidylglycerol (cardiolipin)

D’Arrigo, Paola; Ferra, Lorenzo de; Pedrocchi-Fantoni, Giuseppe; Scarcelli, Domenico; Servi, Stefano De; Strini, Alberto

doi:10.1039/p19960002657

Cited by 20 publications

(47 citation statements)

References 26 publications

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“…Characterization of several PLD enzymes isolated from cultures of Streptomyces species has been previously reported (47,48). All of these enzymes appear to be bona fide PLD, exhibiting specificity for a broad range of substrates, and an inherent catalytic promiscuity, which includes the ability to synthesize cardiolipin in vitro.…”

Section: Discussionmentioning

confidence: 99%

A Eukaryote-like Cardiolipin Synthase Is Present in Streptomyces coelicolor and in Most Actinobacteria

Sandoval-Calderón

Geiger

Guan

et al. 2009

Journal of Biological Chemistry

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Cardiolipin (CL) is an anionic membrane lipid present in bacteria, plants, and animals, but absent from archaea. It is generally thought that bacteria use an enzyme belonging to the phospholipase D superfamily as cardiolipin synthase (Cls) catalyzing a reversible phosphatidyl group transfer from one phosphatidylglycerol (PG) molecule to another PG to form CL and glycerol. In contrast, in eukaryotes a Cls of the CDP-alcohol phosphatidyltransferase superfamily uses cytidine diphosphate-diacylglycerol (CDP-DAG) as the donor of the phosphatidyl group, which is transferred to a molecule of PG to form CL. Searching the genome of the actinomycete Streptomyces coelicolor A3(2) we identified a gene coding for a putative Cls of the CDP-alcohol phosphatidyltransferase superfamily (Sco1389). Here we show that expression of Sco1389 in a CL-deficient Rhizobium etli mutant restores CL formation. In an in vitro assay Sco1389 condenses CDP-DAG with PG to form CL and therefore catalyzes the same reaction as eukaryotic cardiolipin synthases. This is the first time that a CDP-alcohol phosphatidyltransferase from bacteria is shown to be responsible for CL formation. The broad occurrence of putative orthologues of Sco1389 among the actinobacteria suggests that CL synthesis involving a eukaryotic type Cls is common in actinobacteria.

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Section: Discussionmentioning

confidence: 99%

A Eukaryote-like Cardiolipin Synthase Is Present in Streptomyces coelicolor and in Most Actinobacteria

Sandoval-Calderón

Geiger

Guan

et al. 2009

Journal of Biological Chemistry

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“…Both of these products were separated by silica gel chromatography and the structures were confirmed by NMR spectroscopy. The phosphates were individually subjected to hydrogenolysis with 10% Pd/C at 50 psi in tetrahydrofuran at room temperature to obtain tetramyristoyl cardiolipin [1] and 1,2-isomer of cardiolipin [2], respectively, which were immediately converted to ammonium salt with the addition of ammonia. Alternatively, the crude phosphate mixture was subjected to hydrogenolysis and the products were separated at the final stage.…”

Section: Resultsmentioning

confidence: 99%

“…1 (2 · 50 mL), brine (2 · 50 mL), dried over Na 2 SO 4 , concentrated in vacuo and the oily residue 4 (10.84 g) was dried in a desiccator for 8 h and used as such in the next reaction. A solution of the above phosphite 4, glycerol (10.84 g, 14.35 mmol), pyridine (8.75 mL, 108.4 mmol) and Et 3 N (9.4 mL, 71.7 mmol) in CH 2 Cl 2 (150 mL) was cooled to -40°C and pyridinium tribromide (6.88 g, 21.52 mmol) was added.…”

Section: Methodsmentioning

confidence: 99%

“…Selective phosphorylation of the primary alcohol group of PG with PA, either by a semi-synthetic (by enzymes) method [1] or by condensation of PG or 2-O-protected glycerols with PA in the presence of 2,4,6-triisopropylbenzenesulfonyl chloride [2][3][4][5], will result in protected cardiolipin. 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].…”

Section: Introductionmentioning

confidence: 99%

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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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“…Selective phosphorylation of the primary alcohol group of PG with PA either by a semisynthetic method (by enzymes) (12) or by condensation of PG or 2-O-protected glycerols with PA in the presence of 2,4,6-triisopropylbenzenesulfonyl chloride (13)(14)(15)(16) will result in protected CL. Other synthetic approaches describe the use of phosphorylating agents such as cyclic enediol pyrophosphates (17)(18)(19), silver salts of PA (20)(21)(22), phosphorus oxychloride (23), and 2-chlorophenyl phosphorodi-(1,2,4-triazolide) (24).…”

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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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Enzyme-mediated synthesis of two diastereoisomeric forms of phosphatidylglycerol and of diphosphatidylglycerol (cardiolipin)

Cited by 20 publications

References 26 publications

A Eukaryote-like Cardiolipin Synthase Is Present in Streptomyces coelicolor and in Most Actinobacteria

A Eukaryote-like Cardiolipin Synthase Is Present in Streptomyces coelicolor and in Most Actinobacteria

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

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

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