Characterization of the glycosyltransferase activity of DesVII: Analysis of and implications for the biosynthesis of macrolide antibiotics

Journal of the American Chemical Society

Volumn 126, Issue 21, 2004, Pages 6534-6535

  Borisova, Svetlana A ^a   Zhao, Lishan ^a   Melançon III, Charles E ^a   Kao, Chai Lin ^a   Liu, Hung Wen ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

GENE PRODUCT; GLYCOSYLTRANSFERASE; MACROLIDE; METHYMYCIN; PIKROMYCIN; PROTEIN DESVII; UNCLASSIFIED DRUG;

ANTIBIOTIC BIOSYNTHESIS; ARTICLE; CARBOXY TERMINAL SEQUENCE; CATALYSIS; DRUG ACTIVITY; DRUG STRUCTURE; ENZYME ACTIVITY; ESCHERICHIA COLI; GLYCOSYLATION; NONHUMAN; PROTEIN FUNCTION; STREPTOMYCES VENEZUELAE; STRUCTURE ANALYSIS;

ANTI-BACTERIAL AGENTS; GLYCOSYLATION; GLYCOSYLTRANSFERASES; MACROLIDES; MOLECULAR STRUCTURE; STREPTOMYCES;

EID: 2542527641     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja049967j     Document Type: Article

References (21)

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10. The known examples include GtfB, GtfC, GtfD, GtfE in the vancomycin and chloroeremomycin pathways: Losey, H. C.; Peczuh, M. W.; Chen, Z.; Eggert, U. S. ; Dong, S. D.; Pelczer, I.; Kahne, D.; Walsh, C. T. Biochemistry 2001, 40, 4745-4755.
11. The known example is NovM in the novobiocin pathway: Albermann, C.; Soriano, A.; Jiang, J.; Vollmer, H.; Biggins, J. B.; Barton, W. A.; Lesniak, J. ; Nikolov, D. B.; Thorson, J. S. Org. Lett. 2003, 5, 933-936.
12. Xue, Y.; Zhao, L.; Liu, H.-w.; Sherman, D. H. Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 12111-12116.
13. Des VII belongs to the GT-B superfamily of glycosyltransferases based on the sequence comparison to representative glycosyltransferases with known crystal structures (Hu, Y. N.; Walker, S. Chem. Biol. 2002, 9, 1287-1296). It shares high sequence homology to glycosyltransferases involved in the biosynthesis of macrolide antibiotics, such as OleG1 and OleG2 of the oleandomycin pathway in Streptomyces antibioticus (50.5% and 53.5% identity, respectively), TylM2 of the tylosin pathway in Streptomyces fradiae (51.8%), and EryCIII of the erythromycin pathway in Saccharopolyspora erythraea (50.7%). Des VII also exhibits varied sequence similarity to GtfB, C, D, E (18.8-20.9%), and NovM (32.6%).
14. Bierman, M.; Logan, R.; O'Brien, K.; Seno, E. T.; Rao, R. N.; Schoner, B. E. Gene 1992, 116, 43-49.
15. Isolation and characterization of macrolides in S. venezuelae can be found in: Cane, D. E.; Lambalot, R. H.; Prabhakaran, P. C.; Ott, W. R. J. Am. Chem. Soc. 1993, 115, 522-526.
16. For experimental details, see the Supporting Information.
17. Zhao, L.; Borisova, S.; Yeung, S.-M.; Liu, H.-w. J. Am. Chem. Soc. 2001, 123, 7909-7910.
18. Prelog, V.; Gold, A. M.; Talbot, G.; Zamojski, A. Helv. Chim. Acta 1962, 45, 4-7.
19. A few glycosyltransferases responsible for resistance and self-resistance to macrolide antibiotics had been characterized, such as OleD and OleI from the oleandomycin producer S. antibioticus: (a) Quirós, L. M.; Carbajo, R. J.; Braña, A. F.; Salas, J. A. J. Biol. Chem. 2000, 275, 11713-11720.
20. (b) Quirós, L. M.; Salas, J. A. J. Biol. Chem. 1995, 270, 18234-18239. However, in these cases the enzymes catalyze the attachment of glucose to the sugar appendage of macrolide, not onto aglycon directly.
21. A few examples of Des VIII homologues include EryCII of the erythromycin pathway in S. erythraea (36% identity), TylMIII of the tylosin pathway in S. fradiae (42%), and DnrQ of the daunorubicin pathway in Streptomyces peucetius (42%).