L-α-phosphatidyl-D-myo-inositol 3,5-bisphosphate: Total synthesis of a new inositol phospholipid via myo-inositol orthoacetate

Tetrahedron Letters

Volumn 39, Issue 37, 1998, Pages 6769-6772

  Riley, Andrew M ^a   Potter, Barry V L ^a  

^a University of Bath   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

PHOSPHATIDYLINOSITOL; PHOSPHATIDYLINOSITOL 3,5 BISPHOSPHATE; UNCLASSIFIED DRUG;

ARTICLE; LIPID BILAYER; METHODOLOGY; NONHUMAN; PHOSPHOLIPID SYNTHESIS; PHOSPHORYLATION; REACTION ANALYSIS; SIGNAL TRANSDUCTION; STEREOCHEMISTRY;

ALIA;

EID: 0032505203     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01422-1     Document Type: Article

References (19)

1. 1. For reviews see: (a) Divecha, N. and Irvine, R. F. Cell 1995, 80, 269-278;
2. (b) De Camilli, P.; Emr, S. D.; McPherson, P. S., Novick, P. Science 1996, 271, 1533-1539.
3. 2. Whiteford, C. C.; Brearley, C. A. and Ulug, E. T. Biochem. J. 1997, 323, 597-601.
4. 3. Dove, S. K.; Cooke, F.T.; Douglas, M. R.; Sayers, L. G.; Parker, P. J. and Mchell, R. H. Nature 1997, 390, 187-192.
5. 4. Hinchliffe, K. and Irvine, R. F. Nature 1997, 390, 123-124.
6. 5. Garrett, S. W.; Liu, C.; Riley, A. M. and Potter, B. V. L. J. Chem. Soc. Perkin Trans. 1 1998, 1367-1368.
7. f 0.36 (EtOAc / hexane 1:3), mp 77.5 - 78.5°C (from hexane). All new compounds exhibited satisfactory spectroscopic and analytical data.
8. 7. Gilbert, I. H.; Holmes, A. B.; Pestchanker, M. J. and Young, R. C. Carbohydr. Res. 1992, 234, 117-130.
9. 8. Mills, S. J. and Potter, B. V. L. J. Chem. Soc. Perkin Trans. 1 1997, 1279-1286.
10. 9. Purchased from Aldrich and recrystallised once from ether / hexane before use. The enantiomer, (S)-(+)-5-oxo-2-tetrahydrofurancarboxylic [(S)-(+)-TOF] acid, also available from Aldrich, has been used as a chiral derivatising reagent for alcohols (Doolittle, R. E. and Heath, R. R. J. Org. Chem. 1984, 49, 5041-5050). (S)-(+)-TOF esters have also been employed for the optical resolution of (±)-4-benzyloxytetrahydrofuran-3-ol (Altenbach, H.-J. and Wolf, E. Tetrahedron: Asymmetry 1993, 4, 2155-2158).
11. 9. Purchased from Aldrich and recrystallised once from ether / hexane before use. The enantiomer, (S)-(+)-5-oxo-2-tetrahydrofurancarboxylic [(S)-(+)-TOF] acid, also available from Aldrich, has been used as a chiral derivatising reagent for alcohols (Doolittle, R. E. and Heath, R. R. J. Org. Chem. 1984, 49, 5041-5050). (S)-(+)-TOF esters have also been employed for the optical resolution of (±)-4-benzyloxytetrahydrofuran-3-ol (Altenbach, H.-J. and Wolf, E. Tetrahedron: Asymmetry 1993, 4, 2155-2158).
12. 5).
13. 2O), mp 205-207°C (Gigg, J.; Gigg, R.; Payne, S. and Conant, R. J. Chem. Soc. Perkin Trans. 1 1987, 1757-1762. See also references therein).
14. 2O), mp 205-207°C (Gigg, J.; Gigg, R.; Payne, S. and Conant, R. J. Chem. Soc. Perkin Trans. 1 1987, 1757-1762. See also references therein).
15. 5).
16. 13. Yu, K.-L.; Fraser-Reid, B. Tetrahedron Lett. 1988, 29, 979-982.
17. 14 Dreef, C. E.; Elie, C. J. J.; Hoogerhout, P.; van der Marel, G. A. and van Boom, J. H. Tetrahedron Lett. 1988, 29, 6513-6516.
18. 31P NMR spectrum could not be obtained.
19. -, 40%].