Synthesis of 1,3- and 1,2-diphosphatidylglycerol

Lipids

Volumn 42, Issue 3, 2007, Pages 291-296

  Ahmad, Moghis U ^a,b   Krishna, U Murali ^a,c   Ali, Shoukath M ^a,b   Choudhury, Sreeti ^a   Ahmad, Imran ^a,b  

^a NeoPharm Inc   (United States)

^b Jina Pharmaceuticals Inc   (United States)

^c New River Pharmaceuticals   (United States)

Author keywords

Cardiolipin; Cardiolipin isomer; Diphosphatidylglycerol; Phosphitylation; Phosphonium salt methodology

Indexed keywords

CARDIOLIPIN; PHOSPHITYLATION; PHOSPHONIUM SALT; PYRIDINIUMBROMIDE PERBROMIDE;

AMINES; ISOMERS; PHOSPHATES; SALTS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

PHOSPHOLIPIDS;

1,2 DIPHOSPHATIDYLGLYCEROL; 1,3 DIPHOSPHATIDYLGLYCEROL; CARDIOLIPIN; PHOSPHATIDYLGLYCEROL; PHOSPHONIUM DERIVATIVE; PHOSPHORYLCHOLINE; PYRIDINIUM DERIVATIVE; TRIETHYLAMINE; UNCLASSIFIED DRUG;

ARTICLE; ELECTROSPRAY MASS SPECTROMETRY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; OPTICAL ROTATION; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SYNTHESIS;

CARDIOLIPINS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; MAGNETIC RESONANCE SPECTROSCOPY; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SPECTROSCOPY, FOURIER TRANSFORM INFRARED;

EID: 34247490152     PISSN: 00244201     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11745-007-3020-1     Document Type: Article

References (19)

1. Arrigo PD, Ferra LD, Fantoni GP, Scarcelli D, Servi S, Strini A (1996) Enzyme-mediated synthesis of two diastereoisomeric forms of phosphatidylglycerol and of diphosphatidylglycerol (cardiolipin). J Chem Soc Perkin Trans 1(21):2657-2660
2. Keana JFW, Shimiju M, Jernstedt KK (1986) A short, flexible route to symmetrically and unsymmetrically substituted diphosphatidylglycerols (cardiolipin). J Org Chem 51:2297-2299
3. Mishina IM, Vasilenko AE, Stepanov AE, Shvets VI (1987) Studies on complex lipids. Synthesis of diphosphatidylglycerol (cardiolipin) with unsaturated fatty acids. Bioorg Khim 13:1110-1115
4. Mishina IM, Vasilenko AE, Stepanov AE, Shvets VI (1984) Study of lipids. Synthesis of phosphatidylglycerol and diphosphatidylglycerol. Zh Org Khim 20:985-988
5. Mishina IM, Vasilenko AE, Stepanov AE, Shvets VI (1985) Synthesis of diphosphatidylglycerol (cardiolipin) with unsaturated fatty acids. Bioorg Khim 11:992-994
6. Ioannou PV, Marecek JF (1986) Studies on the chemical synthesis and stability of cardiolipins and related compounds. Chem Chorn 15:205-220
7. Ramirez F, Ioannou PV, Marecek JF, Dodd GH, Golding BT (1977) Synthesis of phospholipids by means of cyclic enediol pyrophosphates. Tetrahedron 33:599-608
8. Ramirez F, Ioannou PV, Marecek JF, Golding BT, Dodd GH (1976) Application of cyclic enediol pyrophosphates to the synthesis of phospholipids. Diphosphatidylglycerol (cardiolipin). Synthesis 11:769-770
9. Inoue K, Nojima S (1968) Immunochemical studies of phosoholipids. II. Synthesis of cardiolipin and its analogues. Chem Pharm Bull 16:76-81
10. Inoue K, Nojima S (1963) On the cardiolipin analogues. Synthesis of dipalmitoyl-D,L-α-glycerylphosphoryl-propanol sodium salt and bis(dipalmitoyl-D,L-α-glycerylphosphoryl)-1,3-propanediol disodium salt. Chem Pharm Bull 11:1150-1156
11. Saunders RM, Schwarz HP (1966) Synthesis of phosphatidylglycerol and diphosohatidylglycerol. J Am Chem Soc 88:3844-3847
12. Duralski AA, Spooner PJR, Rankin SE, Watts A (1998) Synthesis of isotopically labelled cardiolipins. Tetrahedron Lett 39:11607-1610
13. Krishna UM, Ahmad MU, Ahmad I (2004) Phosphoramidite approach for the synthesis of cardiolipin. Tetrahedron Lett 45:2077-2079
14. Lin Z, Ahmad MU, Ali SM, Ahmad I (2004) An efficient and novel method for the synthesis of cardiolipin and its analogs. Lipids 39:285-290
15. Krishna UM, Ahmad MU, Ali SM, Ahmad I (2004) A short, concise route to diphosphatidylglycerol (cardiolipin) and its variants. Lipids 39:595-600
16. Browne JE, Driver MJ, Russel JC, Sammes PG (2000) Preparation of phospholipid analogues using the phosphoramidite route. J Chem Soc Perkin Trans 1(5):653-657
17. Beaucage SL, Iyer RP (1993) The synthesis of specific ribonucleotides and unrealated phosphorylated biomolecules by the phosphoramidite method. Tetrahedron 49:10441-10488
18. Watanaba Y, Hirofuji H, Ozaki S (1994) Synthesis of a phosphatidylinositol 3, 4, 5-triphosphate. Tetrahedron Lett 35:123-124
19. Watanaba Y, Nakamura T, Mitsumoto H (1997) Protection of phosphate with the 9-fluorenylmethyl group. Synthesis of unsaturated-acyl phosphatidylinositol 4, 5-bisphosphate. Tetrahedron Lett 38:7407-7410