Convenient synthesis of 3- and 6-deoxy-d-myo-inositol phosphate analogues from (+)-epi- and (-)-vibo-quercitols

Bioorganic and Medicinal Chemistry Letters

Volumn 16, Issue 19, 2006, Pages 5238-5243

  Ogawa, Seiichiro ^a   Tezuka, Yoji ^a  

^a KEIO UNIVERSITY   (Japan)

Author keywords

Deoxyinositol trisphosphate analogues; Inositol phosphates; myo Inositol bioconversion; myo Inositol 1,4,5 trisphosphate

Indexed keywords

FLUORINE DERIVATIVE; INOSITOL PHOSPHATE DERIVATIVE; ISOENZYME; PHOSPHATIDYLINOSITOL 1,4,5 TRISPHOSPHATE; PHOSPHORIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; BIOTRANSFORMATION; CHEMICAL MODIFICATION; CONTROLLED STUDY; DRUG ACTIVITY; DRUG EFFICACY; DRUG SCREENING; DRUG SYNTHESIS; EPIMER; MOUSE; NONHUMAN;

ANIMALS; GLUCOSE-6-PHOSPHATASE; HUMANS; INOSITOL; INOSITOL PHOSPHATES; POLYPHOSPHATES; PROTEIN KINASES; PYRUVATE DEHYDROGENASE (LIPOAMIDE)-PHOSPHATASE; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 33747352007     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2006.06.096     Document Type: Article

References (21)

1. Streb H., Irvine F.R., Berridge M.J., and Schulz I. Nature 306 (1983) 67
2. Berridge M.J., and Irvine R.F. Nature 341 (1989) 197
3. Berridge M.J. Nature 361 (1993) 315 and references cited therein
4. Potter B.V.L., and Lampe O. Angew. Chem., Int. Ed. Engl. 34 (1995) 1933
5. Irvine R.F., and Schell M.J. Nat. Rev. Mol. Cell Biol. 2 (2001) 327
6. Cobb J.E., and Johnson M.R. Tetrahedron 47 (1991) 21
7. Cleophax J., Dubreuil D., Gero S.D., Loupy A., Vieira de Almeida M., Adison D., Da Silva I., and Vass G. Bioorg. Med. Chem. Lett. 5 (1995) 831
8. Takahashi A., Kanbe K., Tamamura T., and Sato K. Anticancer Res. (1999) 3807
9. Ogawa S., Uetsuki S., Tezuka Y., Morikawa T., Takahashi A., and Sato K. Bioorg. Med. Chem. 9 (1999) 1493
10. Ogawa S., Aoyama H., and Tezuka Y. J. Carbohydr. Chem. 20 (2001) 703
11. Ogawa S., Asada M., Ooki Y., Mori M., Itoh M., and Korenaga T. Bioorg. Med. Chem. 13 (2005) 4306
12. Chretien F., Roussel F., Hilly M., Mauger J.-P., and Chapleur Y. J. Carbohydr. Chem. 24 (2005) 549 and references cited therein
13. Takahashi S., Kinoshita T., and Takahashi M. J. Antibiot. 47 (1994) 95
14. Takahashi M., Tanzawa K., and Takahashi S. J. Biol. Chem. 289 (1994) 369
15. In this letter, the nomenclature of cyclitols follows IUPAC-IUB 1973 Recommendations for Cyclitols [Pure. Appl. Chem. 1974, 37, 285].
16. Vieira de Almeida M., Dubreuil D., Cleophax J., Verre-Sebrie C., Pipelier M., Prestat G., Vass G., and Gero S.D. Tetrahedron 55 (1999) 7251 and references cited therein
17. Dubreuil D., Cleophax J., Vieira de Almeida M., Pipelier M., Vass G., and Gero S.D. Tetrahedron 55 (1999) 7573 and references cited therein
18. Safrany S.T., Wojcikiewicz R.J.H., Strupish J., Nahorski S.R., Dubreuil D., Cleophax J., Gero S.D., and Potter B.V.L. FEBS Lett. 278 (1991) 252
19. Seewald M.J., Aksoy I.A., Powis G., Fauq A.H., and Kozikowski A.P. J. Chem. Soc., Chem. Commun. (1990) 1638
20. Kozikowski A.P., Ognyanov V.I., Fauq A.H., Nahorski S.R., and Wilcox R.A. J. Am. Chem. Soc. 115 (1993) 4429
21. gem = 14.4 Hz, H-6eq), 1.83-1.79 (m, 2H, 2 × H-2′), 1.39-1.30 (m, 1H, H-6ax).