Chemo-enzymatic Synthesis of both Enantiomers of myo-Inositol 1,3,4,5-tetrakisphosphate

Bioscience, Biotechnology and Biochemistry

Volumn 63, Issue 8, 1999, Pages 1374-1377

  Laumen, Kurt ^a   Ghisalba, Oreste ^a  

^a NOVARTIS PHARMA AG   (Switzerland)

Author keywords

Candida antarctica; D myo inositol 1,3,4,5 tetrakisphosphate; Enzymatic esterification; L myo inositol 1,3,4,5 tetrakisphosphate; Lipase

Indexed keywords

EID: 0000566081     PISSN: 09168451     EISSN: 13476947     Source Type: Journal    
DOI: 10.1271/bbb.63.1374     Document Type: Article

References (18)

1. D. C. Billington, in “The Inositol Phosphates,” 1st Ed., YCH Publishers, New York, USA, 1993.
2. Billington, D. and Baker, R., Synthesis of myo-inositol 1,3,4,5-tetraphosphate and myo-inositol 1,3-bisphosphate. J. Chem. Soc., Chem. Commun., 1011-1013 (1987).
3. Billington, C., Baker, R., Kulagowski, J. J., Mawer, I. M., Vacca, J. P., deSolms, S. J., and Huff, J. R, The total synthesis of myo-inositol phosphates via myoinositol orthoformate. J. Chem. Soc. Perkin Trans. I, 1423-1429 (1989).
4. Dreef, C. E., Tuinman, R. J., Elie, C. J. J., van der Marel, G. A., and van Boom, J. H., Total synthesis of optically active myo-inositol 1,4,5-trisphosphate and myo-inositol 1,3,4,5-tetrakisphosphate. Reel. Trav. Chim. Pays-Bas, 107, 395-397 (1988).
5. Falck, J. R. and Abdali, A., Total synthesis of D-myo-inositol 3,4,5-trisphosphate and 1,3,4,5-tetrakisphosphate. Bioorg. Med. Chem. Lett., 3, 717-720 (1993).
6. Desai, T., Gigg, J., Gigg, R., and Payne, S., The preparation and phosphorylation of 2,5- and Id-2,6-di-O-benzyl-myo-in-ositol. Carbohydr. Res., 288, 65-79 (1992).
7. Ozaki, S., Kondo, Y., Nakahira, H., Yamaoka, S., and Watanabe, Y., Synthesis of D-myo-inositol 1,3,4,5-tetrakisphosphate. Tetrahedron. Lett., 28, 4691-4694 (1987).
8. Watanabe, Y., Oka, A., Shimizu, Y., and Ozaki, S., Easy access of optically active myo-inositol derivatives by enantioselective acylation using a tartaric acid monoester. Tetrahedron. Lett., 31, 2613-2616 (1990).
9. Watanabe, Y., Fujimoto, T., Shinohara, T., and Ozaki, S., A short step synthesis of optically active myo-inositol 1,3,4,5-tetrakis-(phosphate) and myo-inositol l,4,5-tris(phosphate) from 1,3,5-tri-O-benzyl-myo-inositol. J. Chem. Soc., Chem Commun., 428-429 (1991).
10. Gou, D.-M. and Chen, C.-S., An efficient route to D-myo-in-ositol 3,4,5-triphosphate and D-myo-inositol 1,3,4,5-tetrakisphosphate. Tetrahedron. Lett., 33, 721-724 (1992).
11. Gou, D.-M., Liu, Y.-C., and Chen, C.-S., An efficient chemo-en-zymatic access to optically active myo-inositol polyphosphates. Carbohydr. Res., 234, 51-64 (1992).
12. Baudin, G., Glanzer, B., Swaminathan, K., and Vasella, A, A synthesis of Id and lL-myo-inositol 1,3,4,5-tetraphosphate. Helv. Chim. Acta, 71, 1367-1378 (1988).
13. Bruzik, K. and Tsai, M.-D., Efficient and systematic syntheses of enantiomerically pure and regiospecifically protected myo-in-ositols. J. Am. Chem. Soc., 114, 6361-6374 (1992).
14. Schoffers, E., Golebiowski, A., and Johnson, C. R., Enantioselective synthesis through enzymatic asymmetrization. Tetrahedron, 52, 3769-3826 (1996).
15. Wang, Y.-F. and Wong, C.-H., Lipase-catalyzed irreversible transesterification for preparative synthesis of chiral glycerol derivatives. J. Org. Chem., 53, 3127-3129 (1988).
16. Arbuzov, B. A., Kadyrov, R. A., Klochkov, V. V., Arshinova, R. P., and Aganov, A. V., Spatial structure of phosphorus-containing heterocycles. Izv. Akad. Nauk SSSR, Ser. Khim., 3, 588-593 (1982).
17. Watanabe, Y., Komoda, Y., Ebisuya, K., and Ozaki, S., An efficient phosphorylation method using a new phosphitylating agent, 2-diethylamino-l,3,2-benzodioxaphosphepane. Tetrahedron Lett., 31, 255-256 (1990).
18. Laumen, K. and Ghisalba, O., Preparative-scale chemo-enzymat-ic synthesis of optically pure D-myo-inositol-l-phosphate. Biosci. Biotechnol. Biochem., 58, 2046-2049 (1994).