Probing the regiospecificity of enzyme-catalyzed steroid glycosylation

Organic Letters

Volumn 14, Issue 21, 2012, Pages 5424-5427

  Zhou, Maoquan ^a   Hou, Yanpeng ^a   Hamza, Adel ^b   Zhan, Chang Guo ^b   Bugni, Tim S ^a   Thorson, Jon S ^b  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

^b University of Kentucky   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DIGOXIGENIN; DIGOXIGENIN 12 O BETA D GLUCOSIDE; DIGOXIGENIN 12-O-BETA-D-GLUCOSIDE; DRUG DERIVATIVE; GLUCOSIDE; GLYCOSYLTRANSFERASE; STEROID;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; DRUG SCREENING; GLYCOSYLATION; HUMAN; METABOLISM; NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM; SYNTHESIS;

CATALYSIS; DIGOXIGENIN; DRUG SCREENING ASSAYS, ANTITUMOR; GLUCOSIDES; GLYCOSYLATION; GLYCOSYLTRANSFERASES; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; STEREOISOMERISM; STEROIDS;

EID: 84868353545     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol3024924     Document Type: Article

References (45)

1. Newman, R. A.; Yang, P.; Pawlus, A. D.; Block, K. I. Mol. Interv. 2008, 8, 36-49
2. Prassas, I.; Diamandis, E. P. Nat. Rev. Drug Discovery 2008, 7, 926-935
3. Vaklavas, C.; Chatzizisis, Y. S.; Tsimberidou, A. M. Pharmacol. Ther. 2011, 130, 177-190
4. Gao, H.; Popescu, R.; Kopp, B.; Wang, Z. Nat. Prod. Rep. 2011, 28, 953-969
5. Agrawal, A. A.; Petschenka, G.; Bingham, R. A.; Weber, M. G.; Rasmann, S. New Phytol. 2012, 194, 28-45
6. Yang, E. H.; Shah, S.; Criley, J. M. Am. J. Med. 2012, 125, 337-343
7. Schoner, W.; Scheiner-Bobis, G. Am. J. Physiol. Cell Physiol. 2007, 293, C509-36
8. Suhail, M. J. Clin. Med. Res. 2010, 2, 1-17
9. Mijatovic, T.; Dufrasne, F.; Kiss, R. Curr. Med. Chem. 2012, 19, 627-646
10. Hauck, C.; Frishman, W. H. Cardiol. Rev. 2012, 20, 130-138
11. Langenhan, J. M.; Peters, N. R.; Guzei, I. A.; Hoffmann, F. M.; Thorson, J. S. Proc. Natl. Acad. Sci. U.S.A. 2005, 102, 12305-12310
12. Langenhan, J. M.; Engle, J. M.; Slevin, L. K.; Fay, L. R.; Lucker, R. W.; Smith, K. R.; Endo, M. M. Bioorg. Med. Chem. Lett. 2008, 18, 670-673
13. Hutchinson, C. R.; Shekhani, M. S.; Prudent, J. R. U.S. Patent 2011, 20110319350.
14. Gantt, R. W.; Goff, R. D.; Williams, G. J.; Thorson, J. S. Angew. Chem., Int. Ed. 2008, 47, 8889-8892
15. Gantt, R. W.; Peltier-Pain, P.; Cournoyer, W. J.; Thorson, J. S. Nat. Chem. Biol. 2011, 7, 685-691
16. Yang, M.; Proctor, M. R.; Bolam, D. N.; Errey, J. C.; Field, R. A.; Gilbert, H. J.; Davis, B. G. J. Am. Chem. Soc. 2005, 127, 9336-9337
17. Williams, G. J.; Zhang, C.; Thorson, J. S. Nat. Chem. Biol. 2007, 3, 657-662
18. Williams, G. J.; Goff, R. D.; Zhang, C.; Thorson, J. S. Chem. Biol. 2008, 15, 393-401
19. Seger, C.; Godejohann, M.; Tseng, L.; Spraul, M.; Girtler, A.; Sturm, S.; Stuppner, H. Anal. Chem. 2005, 77, 878-885
20. Motti, C. A.; Freckelton, M. L.; Tapiolas, D. M.; Willis, R. H. J. Nat. Prod. 2009, 72, 290-294
21. Castro, A.; Moco, S.; Coll, J.; Vervoort, J. J. Nat. Prod. 2010, 73, 962-965
22. Elderfield, R. C.; Uhle, F. C.; Fried, J. J. Am. Chem. Soc. 1947, 69, 2235-2236
23. Kihara, M.; Yoshioka, K.; Kitatsuji, E.; Hashimoto, T.; Fullerton, D.t S.; Rohrer, D. C. Steroids 1983, 42, 37-54
24. Ooi, Y.; Hasimoto, T.; Mitsuo, N.; Satoh, T. Tetrahedron Lett. 1984, 25, 2241-2244
25. Quirós, L. M.; Carbajo, R. J.; Salas, J. A. FEBS Lett. 2000, 476, 186-189
26. Quirós, L. M.; Carbajo, R. J.; Braña, A. F.; Salas, J. A. J. Biol. Chem. 2000, 275, 11713-11720
27. Bolam, D. N.; Roberts, S.; Proctor, M. R.; Turkenburg, J. P.; Dodson, E. J.; Martinez-Fleites, C.; Yang, M.; Davis, B. G.; Davies, G. J.; Gilbert, H. Proc. Natl. Acad. Sci. U.S.A. 2007, 104, 5336-5341
28. Zhou, M.; Thorson, J. S. Org. Lett. 2011, 13, 2786-2788
29. Kasai, R.; Suzuo, M.; Asakawa, J.; Tanaka, O. Tetrahedron Lett. 1977, 2, 175-178
30. Taki, T.; Kuroyanagi, M.; Yoshioka, H.; Handa, S. J. Biochem. 1992, 111, 614-619
31. Tori, K.; Ishii, H.; Wolkowski, Z. W.; Chachaty, C.; Sangaré, M.; Piriou, F.; Lukacs, G. Tetrahedron Lett. 1973, 14, 1077-1080
32. Yoshiaki, K.; Ayano, K. Collect. Czech. Chem. Commun. 1998, 63, 1663-1670
33. Ye, M.; Han, J.; Guo, H.; Guo, D. Magn. Reson. Chem. 2002, 40, 786-788
34. and Brown, L.; Boutagy, J.; Thomas, R. Arzneim.-Forsch. 1981, 31, 1059-10604
35. For the chemical synthesis of the 3,12-diglucoside of digoxigenin: Makarevich, I. F Pharm. Chem. J. 1969, 5, 266-269
36. Makarevich, I. F. Khimiya Prirodnykh Soedinenii 1971, 7, 45-46
37. Krenn, L.; Kopp, B.; Deim, A.; Robien, W.; Kubelka, W. Planta Med. 1994, 60, 63-69
38. Ye, M.; Dai, J.i; Guo, H.; Cui, Y.; Guo, D. Tetrahedron Lett. 2002, 43, 8535-8538
39. Ye, M.; Han, J.; Guo, H.; Guo, D. Magn. Reson. Chem. 2002, 40, 786-788
40. Wang, H. Y.; Xin, W.; Zhou, M.; Stueckle, T. A.; Rojanasakul, Y.; O'Doherty, G. A. ACS Med. Chem. Lett. 2011, 2, 73-78
41. Rashan, L. J.; Franke, K.; Khine, M. M.; Kelter, G.; Fiebig, H. H.; Neumann, J.; Wessjohann, L. A. J. Ethnopharmacol. 2011, 134, 781-8
42. Ogawa, H.; Shinoda, T.; Cornelius, F.; Toyoshima, C. Proc. Natl. Acad. Sci. U.S.A. 2009, 106, 13742-13747
43. Katz, A.; Lifshitz, Y.; Bab-Dinitz, E.; Kapri-Pardes, E.; Goldshleger, R.; Tal, D. M.; Karlish, S. J. J. Biol. Chem. 2010, 285, 19582-19592
44. Williams, G. J.; Thorson, J. S. Adv. Enzymol. Relat. Areas. Mol. Biol. 2009, 76, 55-119
45. Gantt, R. W.; Peltier-Pain, P.; Thorson, J. S. Nat. Prod. Rep. 2011, 28, 1811-1853