Conformational restraint is a critical determinant of unnatural nucleotide recognition by protein kinases

Bioorganic and Medicinal Chemistry Letters

Volumn 12, Issue 21, 2002, Pages 3223-3227

  Ulrich, Scott M ^a   Sallee, Nathan A ^b   Shokat, Kevan M ^a,c  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

^c UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

MITOGEN ACTIVATED PROTEIN KINASE; N 4 (BENZYL)AICAR TRIPHOSPHATE; N 4 (BENZYL)RIBAVIRIN TRIPHOSPHATE; NUCLEOTIDE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG CONFORMATION; DRUG SCREENING; DRUG SPECIFICITY; DRUG SYNTHESIS; ENZYME ACTIVE SITE; ENZYME SUBSTRATE; HYDROGEN BOND; STRUCTURE ACTIVITY RELATION;

ADENOSINE TRIPHOSPHATE; HUMANS; HYDROGEN BONDING; MITOGEN-ACTIVATED PROTEIN KINASES; MOLECULAR CONFORMATION; MUTATION; NUCLEOTIDES; P38 MITOGEN-ACTIVATED PROTEIN KINASES; PROTEIN KINASES; RIBAVIRIN; STRUCTURE-ACTIVITY RELATIONSHIP; SUBSTRATE SPECIFICITY; TYROSINE;

EID: 0037020764     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(02)00616-9     Document Type: Article

References (34)

1. Pawson T., Nash P. Genes. Dev. 14:2000;1027.
2. Hunter T. Cell. 100:2000;113.
3. Cohen P. Trends. Biochem. Sci. 25:2000;596.
4. Songyang Z., Blechner S., Hoagland N., Hoekstra M.F., Piwnica-Worms H., Cantley L.C. Curr. Biol. 4:1994;973.
5. Songyang Z., Lu K.P., Kwon Y.T., Tsai L.H., Filhol O., Cochet C., Brickey D.A., Soderling T.R., Bartleson C., Graves D.J., DeMaggio A.J., Hoekstra M.F., Blenis J., Hunter T., Cantley L.C. Mol. Cell. Biol. 16:1996;6486.
6. Songyang Z., Cantley L.C. Methods Mol. Biol. 87:1998;87.
7. Obata T., Yaffe M.B., Leparc G.G., Piro E.T., Maegawa H., Kashiwagi A., Kikkawa R., Cantley L.C. J. Biol. Chem. 275:2000;36108.
8. Hawkins J., Zheng S., Frantz B., LoGrasso P. Arch. Biochem. Biophys. 382:2000;310.
9. Fukunaga R., Hunter T. Embo. J. 16:1997;1921.
10. Lock P., Abram C.L., Gibson T., Courtneidge S.A. EMBO J. 17:1998;4346.
11. Alaimo P.J., Shogren-Knaak M.A., Shokat K.M. Curr. Opin. Chem. Biol. 5:2001;360.
12. Shogren-Knaak M.A., Alaimo P.J., Shokat K.M. Annu. Rev. Cell. Dev. Biol. 17:2001;405.
13. Bishop A., Buzko O., Heyeck-Dumas S., Jung I., Kraybill B., Liu Y., Shah K., Ulrich S., Witucki L., Yang F., Zhang C., Shokat K.M. Annu. Rev. Biophys. Biomol. Struct. 29:2000;577.
14. Witucki L.A., Huang X., Shah K., Liu Y., Kyin S., Eck M.J., Shokat K.M. Chem. Biol. 9:2002;25.
15. Shah K., Shokat K.M. Chem. Biol. 9:2002;35.
16. Habelhah H., Shah K., Huang L., Burlingame A.L., Shokat K.M., Ronai Z. J. Biol. Chem. 276:2001;18090.
17. Habelhah H., Shah K., Huang L., Ostareck-Lederer A., Burlingame A.L., Shokat K.M., Hentze M.W., Ronai Z. Nat. Cell. Biol. 3:2001;325.
18. Chitu V., Demydenko D., Toth G.K., Hegedus Z., Monostori E. Biotechniques. 27:1999;435.
19. Liu Y., Shah K., Yang F., Witucki L., Shokat K.M. Chem. Biol. 5:1998;91.
20. Shah K., Liu Y., Deirmengian C., Shokat K.M. Proc. Natl. Acad. Sci. U.S.A. 94:1997;3565.
21. Ulrich S.M., Buzko O., Shah K., Shokat K.M. Tetrahedron. 56:2000;9495.
22. Sidwell R.W., Robins R.K., Hillyard I.W. Pharmacol. Ther. 6:1979;123.
23. English J.M., Cobb M.H. Trends Pharmacol. Sci. 23:2002;40.
24. Khokhlatchev A., Xu S., English J., Wu P., Schaefer E., Cobb M.H. J. Biol. Chem. 272:1997;11057.
25. Gupta S., Campbell D., Derijard B., Davis R.J. Science. 267:1995;389.
26. Klewer D.A., Zhang P., Bergstrom D.E., Davisson V.J., LiWang A.C. Biochemistry. 40:2001;1518.
27. Zhang P., Johnson W.T., Klewer D., Paul N., Hoops G., Davisson V.J., Bergstrom D.E. Nucleic Acids Res. 26:1998;2208.
28. Voet, D.; Voet, J. G. Biochemistry; 2nd ed.; Wiley: New York, 1995.
29. Adamiak D.A., Saenger W. Acta Crystallogr. B35:1979;924.
30. Wall M., Shim J.H., Benkovic S.J. Biochemistry. 39:2000;11303.
31. Szarek W.A., Pinto B.M., Iwakawa M. Can. J. Chem. 63:1985;2149.
32. Fujii T., Saito T., Hisata H., Shinbo K. Chem. Pharm. Bull. 38:1990;3326.
33. Ludwig J. Acta Biochim. Biophys. Acad. Hung. 16:1981;131.
34. 6) δ 7.89 ppm (t, 1H, J=6.4 Hz), 7.29 ppm (s, 1H), 7.23 ppm (m, 5H), 5.88 ppm (br s, 2H), 5.43 ppm (d, 1H, J=6.4 Hz), 5.32 ppm (d, 1H, J=6.5 Hz), 5.19 ppm (t, 1H, J=4.8 Hz), 5.11 ppm (d, 1H, J=4.4 Hz), 4.33 ppm (d, 2H, J=6.4 Hz), 4.24 ppm (m, 1H), 4.00 ppm (m, 1H), 3.85 ppm (m, 1H), 3.54 ppm (m, 2H).