O-Acetyltransferases for chloramphenicol and other natural products

Antimicrobial Agents and Chemotherapy

Volumn 41, Issue 1, 1997, Pages 1-6

  Murray, Iain A ^a   Shaw, William V ^b  

^a UNIVERSITY OF SHEFFIELD   (United Kingdom)

^b UNIVERSITY OF LEICESTER   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CHLORAMPHENICOL ACETYLTRANSFERASE; NATURAL PRODUCT;

ACETYLATION; DEHALOGENATION; ENZYME ACTIVITY; ENZYME MECHANISM; ENZYME MODIFICATION; ENZYME SPECIFICITY; ENZYME SUBSTRATE; HYDROLYSIS; NUCLEOTIDE SEQUENCE; PRIORITY JOURNAL; REVIEW; STRUCTURE ACTIVITY RELATION;

EID: 0031028172     PISSN: 00664804     EISSN: None     Source Type: Journal    
DOI: 10.1128/aac.41.1.1     Document Type: Review

References (42)

1. Albery, W. J., and J. R. Knowles. 1976. Evolution of enzyme function and the development of catalytic efficiency. Biochemistry 15:5631-5640.
2. Allignet, J., and N. El Solh. 1995. Diversity among the gram-positive acetyltransferases inactivating streptogramin A and structurally related compounds and characterization of a new staphylococcal determinant, vatB. Antimicrob. Agents Chemother. 39:2027-2036.
3. Allignet, J., V. Loncle, P. Mazodier, and N. El Solh. 1988. Nucleotide sequence of a staphylococcal plasmid gene, vgb, encoding a hydrolase inactivating the B components of virginiamycin-like antibiotics. Plasmid 20:271-275.
4. Allignet, J., V. Loncle, C. Simenel, M. Delepierre, and N. El Solh. 1993. Sequence of a staphylococcal gene, vat, encoding an acetyltransferase inactivating the A-type compounds of virginiamycin-like antibiotics. Gene 130: 91-98.
5. Alton, N. E., and D. Vapnek. 1979. Nucleotide sequence of the chloramphenicol resistance transposon Tn9. Nature 282:864-869.
6. Bennett, A. D., and W. V. Shaw. 1983. Resistance to fusidic acid in Escherichia coli mediated by the type I variant of chloramphenicol acetyltransferase. Biochem. J. 215:29-38.
7. Brenner, D. G., and W. V. Shaw. 1985. The use of synthetic oligonucleotides with universal templates for rapid DNA sequencing: results with staphylococcal replicon pC221. EMBO J. 4:561-568.
8. Bunny, K. L., R. M. Hall, and H. W. Stokes. 1995. New mobile gene cassettes containing an aminoglycoside resistance gene, aacA7, and a chloramphenicol resistance gene, catB3, in an integron in pBWH301. Antimicrob. Agents Chemother. 39:686-693.
9. Day, P. J., I. A. Murray, and W. V. Shaw. 1995. Properties of hybrid active sites in oligomeric proteins: kinetic and ligand binding studies with chloramphenicol acelyltransferase trimers. Biochemistry 34:6416-6422.
10. De Meester, C., and J. Rondelet. 1976. Microbial acetylation of M factor of virginiamycin. J. Antibiot. 29:1297-1305.
11. Dicker, I. B., and S. Seetharam. 1992. What is known about the structure and function of the Escherichia coli protein Fir A? Mol. Microbiol. 6:817-823.
12. Downie, J. A. 1989. The nodL gene from Rhizobium leguminasarum is homologous to the acetyltransferases encoded by lacA and cysE. Trends Microbiol. 2:318-324.
13. Dunn, S. M., P. C. E. Moody, J. A. Downie, and W. V. Shaw. 1996. Crystallization and preliminary diffraction studies of NodL, a rhizobial O-acetyltransferase involved in host-specific nodulation of legume roots. Protein Sci. 5:538-541.
14. Ellis, J., C. R. Bagshaw, and W. V. Shaw. 1995. Kinetic mechanism of chloramphenicol acetyltransferase: the role of ternary complex interconversion in rate determination. Biochemistry 34:16852-16859.
15. Gale, E. F., E. Cundliffe, P. E. Reynolds, M. K. Rickmond, and M. J. Waring. 1981. The molecular basis of antibiotic action, 2nd ed., p. 462-468. Wiley, London, United Kingdom.
16. Le Goffic, F., M. Capmau, D. Bonnet, C. Cerceau, C. Soussy, A. Dublanchet, and J. Duval. 1977. Plasmid-mediated pristinamycin resistance. PAC IIA: a new enzyme which modifies pristinamycin IIA. J. Antibiot. 30:665-669.
17. Leslie, A. G. W. 1990. Refined crystal structure of chloramphenicol acetyltransferase at 1.75 Å resolution. J. Mol. Biol. 213:167-186.
18. Leslie, A. G. W., P. C. E. Moody, and W. V. Shaw. 1988. Structure of chloramphenicol acetyltransferase at 1.75Å resolution. Proc. Natl. Acad. Sci. USA 85:4133-4137.
19. Lewendon, A., I. A. Murray, C. Kleanthous, P. M. Cullis, and W. V. Shaw. 1988. Substitutions in the active site of chloramphenicol acetyltransferase; role of a conserved aspartate. Biochemistry 27:7385-7390.
20. Lewendon, A., I. A. Murray, W. V. Shaw, M. R. Gibbs, and A. G. W. Leslie. 1990. Evidence for transition-state stabilisation by serine-148 in the catalytic mechanism of chloramphenicol acetyltransferase. Biochemistry 29: 2075-2080.
21. Lewendon, A., and W. V. Shaw. 1993. Transition state stabilization by chloramphenicol acetyltransferase. Role of a water molecule bound to threonine 174. J. Biol. Chem. 268:20997-21001.
22. Lewendon, A., I. A. Murray, W. V. Shaw, M. R. Gibbs, and A. G. W. Leslie. 1994. Replacement of catalytic histidine-195 of chloramphenicol acetyltransferase: evidence for a general base role for glutamate. Biochemistry 33:1944-1950.
23. Mattevi, A., G. Obmolova, E. Schulze, K. H. Kalk, A. H. Westphal, A. de Kok, and W. G. Hol. 1992. Atomic structure of the cubic core of the pyruvate dehydrogenase multienzyme complex. Science 255:1544-1550.
24. p). Biochemistry 32:3887-3901.
25. Monod, M., S. Mohan, and D. Dubnau. 1987. Cloning and analysis of ermG, a new macrolide-lincosamide-streptogramin B resistance element from Bacillus sphaericus. J. Bacteriol. 169:340-350.
26. Mosher, R. H., D. J. Camp, K. Yang, M. P. Brown, W. V. Shaw, and L. C. Vining. 1995. Inactivation of chloramphenicol by O-phosphorylation. J. Biol. Chem. 27:27000-27006.
27. Murray, I. A., A. R. Hawkins, J. W. Keyte, and W. V. Shaw. 1988. Nucleotide sequence analysis and over-expression of the gene encoding a type III chloramphenicol acetyltransferase. Biochem. J. 252:173-179.
28. Murray, I. A., J. A. Gil, D. A. Hopwood, and W. V. Shaw. 1989. Nucleotide sequence of the chloramphenicol acetyltransferase gene of Streptomyces acrimycini. Gene 85:283-291.
29. Murray, I. A., J. V. Martinez-Suarez, T. J. Close, and W. V. Shaw. 1990. Nucleotide sequences of genes encoding the type II chloramphenicol acetyltransferases of Escherichia coli and Haemophilus influenzae, which are sensitive to inhibition by thiol-reactive reagents. Biochem. J. 272:505-510.
30. Murray, I. A., A. Lewendon, J. A. Williams, P. M. Cullis, W. V. Shaw, and A. G. W. Leslie. 1991. Alternative binding modes for chloramphenicol analogues revealed by site-directed mutagenesis and X-ray crystallography of chloramphenicol acetyltransferase. Biochemistry 30:3763-3770.
31. Murray, I. A., P. A. Cann, P. J. Day, J. P. Derrick, M. J. Sutcliffe, W. V. Shaw, and A. G. W. Leslie. 1995. Steroid recognition by chloramphenicol acetyltransferase: engineering and structural analysis of a high affinity fusidic acid binding site. J. Mol. Biol. 254:993-1005.
32. Murray, I. A., and W. V. Shaw. Unpublished data.
33. Parent, R., and P. H. Roy. 1992. The chloramphenicol acetyltransferase gene of Tn2424: a new breed of CAT. J. Bacteriol. 174:2981-2987.
34. Pongs, O. 1979. Chloramphenicol, p. 26-42. In F. E. Hahn (ed.), Mechanism of action of antibacterial agents. Springer, Berlin, Germany.
35. Raetz, C. R. H., and S. L. Roderick. 1995. A left-handed parallel β helix in the structure of UDP-N-acetylglucosamine acyltransferase. Science 270:997-1000.
36. Rende-Fournier, R., R. LeClercq, M. Galimand, J. Duval, and P. Courvalin. 1993. Identification of the satA gene encoding a streptogramin A acetyltransferase in Enterococcus faecium BM4145. Antimicrob. Agents Chemother. 37:1896-1903.
37. Shaw, W. V. 1983. Chloramphenicol acetyltransferase: enzymology and molecular biology. Crit. Rev. Biochem. 14:1-46.
38. Shaw, W. V. 1992. Chemical anatomy of antibiotic resistance: chloramphenicol acetyltransferase. Sci. Prog. (Oxford) 76:565-580.
39. Shaw, W. V., and A. G. W. Leslie. 1991. Chloramphenicol acetyltransferase. Annu. Rev. Biophys. Biophys. Chem. 20:363-386.
40. Tennigkeit, J., and H. Matzura. 1991. Nucleotide sequence analysis of a chloramphenicol-resistance determinant from Agrobacterium tumefaciens and identification of its gene product. Gene 98:113-116.
41. Toriya, M., M. Sakakibara, K. Matsushita, and T. Morohoshi. 1992. Nucleotide sequence of the 6′-N-acetyltransferase [AAC(6′)] determinant of Serratia SP45. Chem. Pharm. Bull. 40:2473-2477.
42. Wick, M. J., D. W. Frank, D. G. Storey, and B. H. Iglewski. 1990. Identification of regB, a gene required for optimal exotoxin A yields in Pseudomonas aeruginosa. Mol. Microbiol. 4:489-497.