Substrate specificity of NovM: Implications for novobiocin biosynthesis and glycorandomization

Organic Letters

Volumn 5, Issue 6, 2003, Pages 933-936

  Albermann, Christoph ^a   Soriano, Aileen ^a   Jiang, Jiqing ^a   Vollmer, Heidi ^a   Biggins, John B ^a   Barton, William A ^b   Lesniak, Jacob ^b   Nikolov, Dimitar B ^b   Thorson, Jon S ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

^b MEMORIAL SLOAN KETTERING CANCER CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

NATURAL PRODUCT; NOVOBIOCIN; NOVOBIOCIN M; NUCLEOTIDE; SUGAR; UNCLASSIFIED DRUG; ANTIINFECTIVE AGENT; GLYCOSIDE;

ARTICLE; BIOSYNTHESIS; DRUG PURIFICATION; ENZYME SPECIFICITY; NONHUMAN; RANDOMIZATION; CHEMISTRY; STREPTOMYCES;

ANTI-BACTERIAL AGENTS; GLYCOSIDES; NOVOBIOCIN; STREPTOMYCES; SUBSTRATE SPECIFICITY;

EID: 0038204472     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0341086     Document Type: Article

References (31)

1. (a) Hooper, D. C.; Wolfson, J. S.; McHugh, G. L.; Winters, M. B.; Swartz, M. N. Antimicrob. Agents Chemother. 1982, 22, 662-671.
2. (b) Maxwell, A. Mol. Microbiol. 1993, 9, 681-686.
3. (c) Maxwell, A. Trends Microbiol. 1997, 5, 102-109.
4. (d) Maxwell, A. Biochem. Soc. Trans. 1999, 27, 48-53.
5. (a) Tsai, F. T.; Singh, O. M.; Skarzynski, T.; Wonacott, A. J.; Weston, S.; Tucker, A.; Pauptit, R. A.; Breeze, A. L.; Poyser, J. P.; O'Brien, R.; Ladbury, J. E.; Wigley, D. B. Proteins 1997, 28, 41-52.
6. (b) Lewis, R. J.; Singh, O, M,; Smith, C. V.; Skarzynski, T.; Maxwell, A.; Wonacott, A. J.; Wigley, D. B. EMBO J 1996, 15, 1412-1420.
7. (a) Steffensky, M.; Li, S.-M.; Heide, L. J. Biol. Chem. 2000, 275, 21754-21760.
8. (b) Chen, H.; Walsh, C. T. Chem. Biol. 2001, 8, 301-312.
9. (c) Pojer, F.; Li, S.-M.; Heide, L. Microbiology 2002, 148, 3901-3911.
10. (a) Steffensky, M.; Muhlenweg, A.; Wang, Z. X.; Li, S.-M.; Heide, L. Antimicrob. Agents Chemother. 2000, 44, 1214-1222.
11. (b) Wang, Z. X.; Li, S.-M.; Heide, L. Antimicrob. Agents Chemother. 2000, 44, 3040-3048.
12. He, X. M.; Liu, H.-w. Annu. Rev. Biochem. 2002, 71, 701-754.
13. Birch, A. J.; Holloway, P. W.; Richards, R. W. Biochim. Biophys. Acta 1962, 57, 143-145.
14. (a) Jiang, J.; Biggins, J. B.; Thorson, J. S. J. Am. Chem. Soc. 2000, 122, 6803-6804.
15. (b) Thorson, J. S.; Hosted, T. J., Jr.; Jiang, J.; Biggins, J. B.; Ahlert, J.; Ruppen, M. Curr. Org. Chem. 2001, 5, 139-167.
16. (c) Jiang, J.; Biggins, J. B.; Thorson, J. S. Angew. Chem., Int. Ed. 2001, 40, 1502-1505.
17. (d) Barton, W. A.; Biggins, J. B.; Lesniak, J.; Jeffrey, P. D.; Jiang, J.; Rajashankar, K. R.; Thorson, J. S.; Nikolov, D. B. Nature Struct. Biol. 2001, 8, 545-551.
18. (e) Barton, W. A.; Biggins, J. B.; Jiang, J.; Thorson, J. S.; Nikolov, D. B. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 13397-13402.
19. (f) Thorson, J. S.; Barton, W. A.; Albermann, C.; Hoffmeister, D.; Nikolov, D. B. ChemBioChem. In press.
20. (g) Jiang, J.; Albermann, C.; Thorson, J. S. Angew Chem., Int. Ed. Submitted for publication.
21. (a) Solenberg, P. J.; Matsushima, P.; Stack, D. R.; Wilkie, S. C.; Thompson, R. C.; Baltz, R. H. Chem. Biol. 1997, 4, 195.
22. (b) Losey, H.; Jiang, J.; Biggins, J. B.; Oberthur, M.; Ye, X.-Y.; Dong, S. D.; Kahne, D.; Thorson, J. S.; Walsh, C. T. Chem. Biol. 2002, 9, 1305-1314.
23. (c) Albermann, C.; Xun-Fu, A.; Jiang, J.; Thorson, J. S. Unpublished.
24. PCR-amplified novM with engineered flanking NdeI/XhoI restriction sites was blunt-end ligated into pBS and the insert sequence confirmed to give plasmid pKMACTW. The corresponding NdeI/XhoI insert bearing novM was cloned into the Nde1/Xho1 site of pET20/22.
25. -1 and stored at -80°C.
26. -1, 305 nm). Retention times: 10 (21.3 min), 25 (17.9 min), 26 (15.5 min), and 27 (18.7 min).
27. Kominek, L. A.; Meyer, H. F. Methods Enzymol. 1975, 43, 502-508.
28. Zhao, Y.; Thorson, J. S. J. Org. Chem. 1998, 63, 7568-7572.
29. m for 16 was estimated by fitting the plot of initial velocity versus substrate concentration to the above equation using the Kaleidograph.
30. 10 541.19, found m/z 542.3 (M + H).
31. Products were tested for antibacterial activity against Streptomyces griseoruber (ATCC). A 10-mL sample of overnight cultures (in YEME broth) was applied to ISP agar plates containing varying amounts of the 1 analogues (0.06 mg/mL to 20 mg/mL). Similar amounts were applied to ISP agar plates containing varying concentrations of 1 or 10. Control plates consisted of ISP agar only. The plates were incubated at 28°C and monitored for growth overnight and after 2 days.