Exploring the substrate promiscuity of drug-modifying enzymes for the chemoenzymatic generation of N-acylated aminoglycosides

ChemBioChem

Volumn 11, Issue 1, 2010, Pages 119-126

  Green, Keith D ^a   Chen, Wenjing ^a   Houghton, Jacob L ^a   Fridman, Micha ^b   Garneau Tsodikova, Sylvie ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

^b TEL AVIV UNIVERSITY   (Israel)

Author keywords

Aminoglycoside acetyltransferases; Antibiotics; Chemoenzymatic acylation; Coenzyme A cosubstrates; Enzymes

Indexed keywords

3 N ACETYL NEOMYCIN B; 3 N N PROPIONYL NEOMYCIN B; 6' N ACETYL NEOMYCIN B; 6' N N PROPIONYL NEOMYCIN B; ACYL COENZYME A; ACYLTRANSFERASE; AMIKACIN; AMINOGLYCOSIDE DERIVATIVE; FRAMYCETIN; GENTAMICIN; KANAMYCIN A; PAROMOMYCIN; SISOMICIN; TOBRAMYCIN; UNCLASSIFIED DRUG;

ACETYLATION; AMINO TERMINAL SEQUENCE; ANTIBACTERIAL ACTIVITY; ARTICLE; BACILLUS SUBTILIS; CARBOXY TERMINAL SEQUENCE; CONTROLLED STUDY; DRUG DESIGN; DRUG POTENCY; DRUG SYNTHESIS; ENZYME KINETICS; ENZYME MODIFICATION; ENZYME SPECIFICITY; ENZYME SYNTHESIS; NONHUMAN; PRIORITY JOURNAL; STEREOCHEMISTRY;

ACETYLATION; ACETYLTRANSFERASES; ACYL COENZYME A; AMINOGLYCOSIDES; ANTI-BACTERIAL AGENTS; KINETICS; PHOSPHOTRANSFERASES (ALCOHOL GROUP ACCEPTOR); SUBSTRATE SPECIFICITY;

BACTERIA (MICROORGANISMS);

EID: 75649101296     PISSN: 14394227     EISSN: 14397633     Source Type: Journal    
DOI: 10.1002/cbic.200900584     Document Type: Article

References (25)

1. B. D. Davis, Microbiol. Rev. 1987, 51, 341.
2. S. Jana, J. K. Deb, Appl. Microbiol. Biotechnol. 2006, 70, 140.
3. M. Hainrichson, I. Nudelman, T. Baasov, Org. Biomol. Chem. 2008, 6, 227.
4. S. Magnet, J. S. Blanchard, Chem. Rev. 2005, 105, 477.
5. J. M. Ogle, D. E. Brodersen, W. M. Clemons, Jr., M. J. Tarry, A. P. Carter, V. Ramakrishnan, Science 2001, 292, 897.
6. Q. Vicens, E. Westhof, Biopolymers 2003, 70, 42.
7. G. D. Wright, A. M. Berghuis, S. Mobashery, Adv. Exp. Med. Biol. 1998, 456, 27.
8. A. Kumar, H. P. Schweizer, Adv. Drug Delivery Rev. 2005, 57, 1486.
9. P. W. K. Woo, H. W. Dion, Q. R. Bartz, Tetrahedron Lett. 1971, 12, 2617.
10. P. W. K. Woo, Tetrahedron Lett. 1971, 12, 2621.
11. P. W. K. Woo, H. W. Dion, Q. R. Bartz, Tetrahedron Lett. 1971, 12, 2625.
12. S. Kondo, K. Hotta, J. Infect. Chemother. 1999, 5, 1.
13. H. Kawaguchi, T. Naito, S. Nakagawa, K. I. Fujisawa, J. Antibiot. 1972, 25, 695.
14. J. Haddad, L. P. Kotra, B. Llano-Sotelo, C. Kim, E. F. Azucena, Jr., M. Liu, S. B. Vakulenko, C. S. Chow, S. Mobashery, J. Am. Chem. Soc. 2002, 124, 3229.
15. I. Nudelman, A. Rebibo-Sabbah, M. Cherniavsky, V. Belakhov, M. Hainrichson, F. Chen, J. Schacht, D. S. Pilch, T. Ben-Yosef, T. Baasov, J. Med. Chem. 2009, 52, 2836.
16. K. Hotta, T. Ogata, J. Ishikawa, M. Okanishi, S. Mizuno, M. Morioka, H. Naganawa, Y. Okami, J. Antibiot. 1996, 49, 682.
17. F. Kobayashi, Y. Saino, T. Koshi, Y. Hattori, Antimicrob. Agents Chemother. 1980, 17, 337.
18. Y. Matsuhashi, T. Yoshida, T. Hara, Y. Kazuno, S. Inouye, Antimicrob. Agents Chemother. 1985, 27, 589.
19. M. Fridman, C. J. Balibar, T. Lupoli, D. Kahne, C. T. Walsh, S. Garneau-Tsodikova, Biochemistry 2007, 46, 8462.
20. K. D. Green, M. Fridman, S. Garneau-Tsodikova, ChemBioChem 2009, 10, 2191.
21. D. D. Boehr, W. S. Lane, G. D. Wright, Chem. Biol. 2001, 8, 791.
22. E. Wolf, A. Vassilev, Y. Makino, A. Sali, Y. Nakatani, S. K. Burley, Cell 1998, 94, 439.
23. M. L. Magalhaes, J. S. Blanchard, Biochemistry 2005, 44, 16275.
24. B. Ostash, A. Saghatelian, S. Walker, Chem. Biol. 2007, 14, 257.
25. M. A. Shahid, M. Siddique, S.-U. Rehman, S. Hameed, A. Hussain, Am. J. Food Technol. 2007, 2, 457.