Optimized synthesis of phosphatidylserine

Amino Acids

Volumn 39, Issue 2, 2010, Pages 367-373

  Guanti, Giuseppe ^a   Banfi, L ^a   Basso, A ^a   Bondanza, L ^a   Guglieri, G ^a   Powles, K ^a   Riva, R ^a  

^a UNIVERSITY OF GENOA   (Italy)

Author keywords

Multicomponent reactions; Phospholipids; Phosphorodiamidites

Indexed keywords

1,2 O DIPALMITOYL SN GLYCERO 3 PHOSPHOSERINE; CHLORIDE; GLYCEROL; IMIDAZOLIUM CHLORIDE; N (BENZYLOXYCARBONYL) SERINE BENZYL ESTER; O BENZYL N,N,N',N' TETRAISOPROPYL PHOSPHORODIAMIDITE; O BENZYL O [2 (BENZYLOXYCARBONYL) 2 (BENZYLOXYCARBONYLAMINO)ETHYL] O (1,2 O DIPALMITOYL SN GLYCERYL) PHOSPHATE; PALLADIUM; PHOSPHATE; PHOSPHATIDYLSERINE; PLATINUM; SATURATED FATTY ACID; SERINE; UNCLASSIFIED DRUG; DIACYLGLYCEROL; IMIDAZOLE; IMIDAZOLE DERIVATIVE; ORGANOPHOSPHORUS COMPOUND;

ACYLATION; AMINO ACID ANALYSIS; AMINO ACID SYNTHESIS; ARTICLE; CATALYST; CONTROLLED STUDY; DEPROTECTION REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOSELECTIVITY; HYDROGENATION; ONE POT SYNTHESIS; OXIDATION; PRIORITY JOURNAL; PROCESS OPTIMIZATION; PROTEIN PURIFICATION;

DIGLYCERIDES; IMIDAZOLES; ORGANOPHOSPHORUS COMPOUNDS; PHOSPHATIDYLSERINES;

EID: 80055002443     PISSN: 09394451     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00726-009-0447-0     Document Type: Article

References (37)

1. Baer E, Maurukas J (1955) Phosphatidyl serine. J Biol Chem 212:25-38
2. Bannwarth W, Trzeciak A (1987) A simple and effective chemical phosphorylation procedure for biomolecules. Helv Chim Acta 70:175-186
3. Blokland A, Honig W, Brouns F, Jolles J (1999) Cognition-enhancing properties of subchronic phosphatidylserine (PS) treatment in middle-aged rats: comparison of bovine cortex PS with egg PS and soybean PS. Nutrition 15:778-783
4. Bruzik KS, Salamonczyk G, Stec WJ (1986) A general method for the synthesis of glycerophospholipids. J Org Chem 51:2368-2370
5. Burgos CE, Ayer DE, Johnson RA (1987) A new, asymmetric synthesis of lipids and phospholipids. J Org Chem 52:4973-4977
6. Chen J, Profit AA, Prestwich GD (1996) Synthesis of photoactivatable 1, 2-o-diacyl-sn-glycerol derivatives of 1-l-phosphatidyl-D-myo-inositol 4, 5-bisphosphate (ptdinsp2) and 3, 4, 5-trisphosphate (ptdinsp3). J Org Chem 61:6305-6312
7. Chen J, Feng L, Prestwich GD (1998) Asymmetric total synthesis of phosphatidylinositol 3-phosphate and 4-phosphate derivatives. J Org Chem 63:6511-6522
8. Claesen CAA, Segers RPAM, Tesser GI (1985) Ar (alk) ylsulfonyl ethyl groups as phosphorus protecting functions. Recl Trav Chim Pays-Bas 104:119-122
9. Dittmer JC, Lester RL (1964) A simple, specific spray for the detection of phospholipids on thin-layer chromatograms. J Lipid Res 5:126-127
10. Dreef CE, Elie CJJ, Hoogerhout P, van der Marel GA, van Boom JH (1988) Synthesis of 1-o-(1, 2-di-o-palmitoyl-sn-glycero-3-phospho)-D-myo-inositol 4, 5-bisphosphate: an analogue of naturally occurring (ptd) ins (4, 5) p2. Tetrahedron Lett 29:6513-6516
11. Dreef-Tromp CM, Lefeber AWM, van der Marel GA, van Boom JH (1992) Synthesis and phosphorylating properties of hydroxyamino acid phosphoramidites. Synthesis, pp 1269-1272
12. Eibl H (1984) Phospholipids as functional constituents of biomembranes. Angew Chem Int Ed Engl 23:257-271
13. Guanti G, Basso A, Banfi L, Bevilacqua E, Bondanza L et al (2004) Efficient chemoenzymatic enantioselective synthesis of diacylglycerols (dag). Tetrahedron Asymmetry 15:2889-2892
14. Hébert N, Just G (1990) Synthesis of phospholipids using an inverse phosphite triester approach. J Chem Soc Chem Commun, pp 1497-1498
15. Hermetter A, Paltauf F, Hauser H (1982) Synthesis of diacyl and alkylacyl glycerophosphoserines. Chem Phys Lipids 30:35-45
16. Inami K, Teshima T, Emura J, Shiba T (1990) Synthesis of lysophosphatidylserine with 19:4 acyl group, as a novel sodium-potassium ATPase inhibitor, in relation to DLIS-2, an endogenous digoxin-like substance. Tetrahedron Lett 31:4033-4036
17. Itaya T, Iida T, Shimizu S, Mizutani A, Morisue M et al (1993) Wittig reaction with N-protected 3-(triphenylphosphonio) alaninates: synthesis of optically active (E) - (2-arylvinyl) glycine derivatives. Chem Pharm Bull 41:252-261
18. King RB, Sundaram PM (1984) Bis (dialkylamino) phosphines. J Org Chem 49:1784-1789
19. Kozikowski AP, Powis G, Fauq AH, Tückmantel W, Gallegos A (1994) Synthesis and biological activity of the D-3-deoxy-3-fluoro and D-3-chloro-3-deoxy analogs of phosphatidylinositol. J Org Chem 59:963-971
20. Lindh I, Stawinski J (1989) A general method for the synthesis of glycerophospholipids and their analogs via H-phosphonate intermediates. J Org Chem 54:1338-1342
21. Martin SF, Josey JA (1988) A general protocol for the preparation of phospholipids via phosphite coupling. Tetrahedron Lett 29:3631-3634
22. Martin SF, Wagman AS (1996) Synthesis and kinetic evaluation of inhibitors of the phosphatidylinositol-specific phospholipase c from Bacillus cereus. J Org Chem 61:8016-8023
23. Martin SF, Josey JA, Wong Y-L, Dean DW (1994) General method for the synthesis of phospholipid derivatives of 1, 2-o-diacyl-snglycerols. J Org Chem 59:4805-4820
24. Mayer TG, Weingart R, Münstermann F, Kawada T, Kurzchalia T et al (1999) Synthesis of labeled glycosyl phosphatidyl inositol (gpi) anchors. Eur J Org Chem, pp 2563-2571
25. Miller PS, Fang KN, Kondo NS, Ts'O POP (1971) Conformation and interaction of dinucleoside mono-and diphosphates, V. Syntheses and properties of adenine and thymine nucleoside alkyl phosphotriesters, the neutral analogs of dinucleoside monophosphates. J Am Chem Soc 93:6657-6665
26. Misiura K, Okruszek A, Pankiewicz K, Stec WJ, Czownicki Z et al (1983) Stereospecific synthesis of chiral metabolites of ifosfamide and their determination in the urine. J Med Chem 26:674-679
27. Ogilvie KK, Theriault NY, Seifert J-M, Pon RT, Nemer MJ (1980) The chemical synthesis of oligoribonucleotides. IX. A comparison of protecting groups in the dichloridite procedure. Can J Chem 58:2686-2693
28. Pepeu G, Marconcini Pepeu I, Amaducci L (1996) A review of phosphatidylserine pharmacological and clinical effects. Is phosphatidylserine a drug for the ageing brain? Pharm Res 33:73-80
29. Prestwich GD, Marecek JF, Mourey RJ, Theibert AB, Ferris CD et al (1991) Tethered ip3. Synthesis and biochemical applications of the 1-o-(3-aminopropyl) ester of inositol (1, 4, 5)-trisphosphate. J Am Chem Soc 113:1822-1825
30. Reddy KK, Saady M, Falck JR, Withed G (1995) Intracellular mediators: synthesis of l-alpha-phosphatidyl-d-myo-inositol 3, 4, 5-trisphosphate and glyceryl ether analogs. J Org Chem 60:3385-3390
31. Smirnov MD, Ford DA, Esmon CT, Esmon NL (1999) The effect of membrane composition on the hemostatic balance. Biochemistry 38:3591-3598
32. van Boeckel CAA, Oltvoort JJ, van Boom JH (1981) Phosphotriester approach to the synthesis of α-glucosylated mono-and diphosphatidyl glycerols: bacterial cell-wall components. Tetrahedron 37:3751-3761
33. van Boeckel CAA, Visser GM, van Boom JH (1985) Synthesis of phosphatidyl-β-glucosyl glycerol containing a dioleoyl diglyceride moiety: application of the tetraisopropyldisiloxane-1, 3-diyl (tips) protecting group in sugar chemistry. Part IV. Tetrahedron 41:4557-4565
34. Wakamiya T, Nishida T, Togashi R, Saruta K, Yasuoka J et al (1996) Preparations of N-alpha-fmoc-o-[(benzyloxy) hydroxyphosphinyl] beta-hydroxy alpha-amino acid derivatives. Bull Chem Soc Jpn 69:465-468
35. Xia J, Hui Y-Z (1997a) The efficient synthesis of mixed diacyl phospholipids with polyunsaturated fatty acid in sn-2 position of glycerol. Tetrahedron Asymmetry 8:3019-3021
36. Xia J, Hui Y-Z (1997b) The stereospecific synthesis of mixed-acid phospholipids with polyunsaturated fatty acid from D-mannitol. Tetrahedron Asymmetry 8:451-458 (Pubitemid 27078165)
37. Yamauchi K, Une F, Tabata S, Kinoshita M (1986) Synthesis of glycerophospholipids containing aminoalkylphosphonic acids. J Chem Soc Perkin Trans 1:765-770