Application of the nucleotidylyltransferase Ep toward the chemoenzymatic synthesis of dTDP-desosamine analogues

ChemBioChem

Volumn 4, Issue 5, 2003, Pages 443-446

  Jiang, Jiqing ^a   Albermann, Christoph ^a   Thorson, Jon S ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

Antibiotics; Enzyme catalysis; Glycorandomization; Glycosyl transferases; Nucleotides

Indexed keywords

DESOSAMINE; GLYCOSYLTRANSFERASE; MACROLIDE; NUCLEOTIDYLTRANSFERASE; NUCLEOTIDYLTRANSFERASE EP; PYRANOSIDE; THYMIDINE DIPHOSPHATE; UNCLASSIFIED DRUG; AMINOSUGAR; GLYCOSIDE; PYRIMIDINE NUCLEOTIDE;

ARTICLE; CATALYSIS; CATALYST; DRUG SYNTHESIS; ENZYME ACTIVITY; ENZYME SPECIFICITY; ENZYME SUBSTRATE COMPLEX; PRIORITY JOURNAL; REACTION ANALYSIS; STRUCTURE ACTIVITY RELATION; BIOSYNTHESIS; CHEMISTRY; ENZYMOLOGY; GENETICS; METABOLISM; SALMONELLA; SYNTHESIS;

AMINO SUGARS; GLYCOSIDES; NUCLEOTIDYLTRANSFERASES; SALMONELLA; SUBSTRATE SPECIFICITY; THYMINE NUCLEOTIDES;

EID: 0038249172     PISSN: 14394227     EISSN: None     Source Type: Journal    
DOI: 10.1002/cbic.200200566     Document Type: Article

References (35)

1. (a) J. S. Thorson, T. J. Hosted Jr., J. Jiang, J. B. Biggins, J. Ahlert, M. Ruppen, Curr. Org. Chem. 2001, 5, 139;
2. (b) Glycosylated Natural Products: J. S. Thorson, T. Vogt in Modern Carbohydrate Chemistry, Benchtop to Clinic (Ed.: C.-H. Wong), Wiley-VCH, Weinheim, Germany, in press.
3. (a) E. H. Flynn, H. W. Murphy, R. E. McMahon, J. Am. Chem. Soc. 1955, 77, 3104;
4. (b) S. Omura, K. Tsuzuki, T. Sunazuka, S. Marui, H. Toyota, N. Inatomi, Z. Itoh, J. Med. Chem. 1987, 30, 1943.
5. (a) M. Delaforge, E. Strtori, D. Mansuy, Chem.-Biol. Interact. 1988, 68, 179;
6. (b) M. Delaforge, P. Ladam, G. Bouille, J. Gharbi-Benarous, M. Jaouen, J.-P. Girault, Chem.-Biol. Interact. 1992, 85, 215;
7. (c) P. Ladam, J. Gharbi-Benarous, M. Delforge, M. R. Van Calsteren, C. K. Jankowski, J.-P. Girault, Bioorg. Med. Chem. 1995, 3, 587.
8. R. P. Gladue, G. M. Bright, R. E. Isaacson, M. F. Newborg, Antimicrob. Agents Chemother. 1989, 33, 277.
9. (a) H. Chen, H. Yamase, K. Murakami, C.-w. Chang, L. Zhao, H.-w. Liu, Biochemistry 2002, 41, 9165;
10. (b) L. Zhao, S. Borisova, S.-M. Yeung, H.-w. Liu, J. Am. Chem. Soc. 2001, 123, 7909;
11. (c) C.-w. Chang, L. H. Zhao, H. Yamase, H.-w. Liu, Angew. Chem. 2000, 112, 2244; Angew. Chem. Int. Ed. 2000, 39, 2160;
12. (c) C.-w. Chang, L. H. Zhao, H. Yamase, H.-w. Liu, Angew. Chem. 2000, 112, 2244; Angew. Chem. Int. Ed. 2000, 39, 2160;
13. (d) S. A. Borisova, L. Zhao, D. H. Sherman, H.-w. Liu, Org. Lett. 1999, 1, 133;
14. (e) L. S. Zhao, J. Ahlert, Y. Q. Xue, J. S. Thorson, D. H. Sherman, H.-w. Liu, J. Am. Chem. Soc. 1999, 121, 9881;
15. (f) L. S. Zhao, N. L. S. Que, Y. Q. Xue, D. H. Sherman, H.-w. Liu, J. Am. Chem. Soc. 1998, 120, 12159;
16. (g) L. S. Zhao, D. H. Sherman, H.-w. Liu, J. Am. Chem. Soc. 1998, 120, 10 256;
17. (h) L. S. Zhao, D. H. Sherman, H.-w. Liu, J. Am. Chem. Soc. 1998, 120, 9374.
18. C.-W. T. Chang, H.-w. Liu, Bioorg. Med. Chem. Lett. 2002, 12, 1493.
19. p') but is more accurately designated Glc-1-P thymidylyltransferase.
20. (a) J. Jiang, J. B. Biggins, J. S. Thorson, J. Am. Chem. Soc. 2000, 122, 6803;
21. (b) J. Jiang, J. B. Biggins, J. S. Thorson, Angew. Chem. 2001, 113, 550; Angew. Chem. Int. Ed. 2001, 40, 1502.
22. (b) J. Jiang, J. B. Biggins, J. S. Thorson, Angew. Chem. 2001, 113, 550; Angew. Chem. Int. Ed. 2001, 40, 1502.
23. (a) W. A. Barton, J. B. Biggins, J. Lesniak, P. D. Jeffrey, J. Jiang, K. R. Rajashankar, J. S. Thorson, D. B. Nikolov, Nat. Struct. Biol. 2001, 8, 545;
24. (b) W. A. Barton, J. B. Biggins, J. Jiang, J. S. Thorson, D. B. Nikolov, Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 13397-13402.
25. (a) C. Albermann, A. Sorianno, J. Jiang, J. B. Biggins, W. A. Barton, J. Lesniak, D. B. Nikolov, J. S. Thorson, Org. Lett. 2003, in press;
26. (b) H. Losey, J. Jiang, J. B. Biggins, M. Oberthur, X.-Y. Ye, S. D. Dong, D. Kahne, J. S. Thorson, C. T. Walsh, Chem. Biol. 2002, 9, 1305.
27. K. C. Nicolaou, R. A. Daines, Y. Ogawa, T. K. Chakraborty, J. Am. Chem. Soc. 1988, 110, 4696.
28. A. K. Ogawa, J. A. DeMattel, G. R. Scarlato, J. E. Tellew, L. S. Chong, R. W. Armstrong, J. Org. Chem. 1996, 61, 6153.
29. (a) H. Redlich, W. Roy, Carbohydr. Res. 1979, 68, 275;
30. (b) S. Hanessian, R. Roy, Can. J. Chem. 1985, 63, 163.
31. p variants and the best conversions (average of three independent assays) are illustrated in Table 1.
32. (a) Handbook of Chemistry and Physics, 82nd ed., (Ed.: D. R. Lide), CRC Press, Boca Raton, 2001, pp. 8-46;
33. (b) H. H. Jaffe, L. D. Freedman, G. O. Doak, J. Am. Chem. Soc. 1953, 75, 2209.
34. Assays at higher pH values were carried out as described (ref. [14]) but with different buffer conditions: 50 mM Tris/HCl, (pH 7, 7.5, 8.5) and 50 mM Tricine/NaOH (pH 9, 9.5, 10, 10.5). The corresponding yield with Glc-1-P at pH 10.5 was > 60% of that observed at pH 8.0.
35. W. A. Barton, J. B. Biggins, J. Jiang, D. B. Nikolov, J. S. Thorson, unpublished data.