Eubacterial arylamine N-acetyltransferases-identification and comparison of 18 members of the protein family with conserved active site cysteine, histidine and aspartate residues

Microbiology

Volumn 147, Issue 5, 2001, Pages 1137-1147

  Payton, Mark ^a   Mushtaq, Adeel ^a   Yu, Tin Wein ^b   Wu, Ling Juan ^c   Sinclair, John ^d   Sim, Edith ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

^b UNIVERSITY OF WASHINGTON   (United States)

^c UNIVERSITY OF OXFORD   (United Kingdom)

^d UNIVERSITY OF OXFORD   (United Kingdom)

Author keywords

Endogenous function; Gene cluster; NAT; Prokaryotic

Indexed keywords

4 AMINOBENZOIC ACID; 4 AMINOBENZOYL GLUTAMATE; AROMATIC AMINE; ARYLAMINE ACETYLTRANSFERASE; ASPARTIC ACID; CYSTEINE; DNA; GLUTAMIC ACID DERIVATIVE; HISTIDINE; HYDRAZINE; ISONIAZID; ORGANIC MATTER; UNCLASSIFIED DRUG; XENOBIOTIC AGENT;

ARTICLE; CONTROLLED STUDY; DECOMPOSITION; DNA LIBRARY; DRUG DETOXIFICATION; DRUG METABOLISM; DRUG STRUCTURE; ENZYME ACTIVE SITE; EUBACTERIUM; EUKARYOTE; GENE CLUSTER; GENE SEQUENCE; GENETIC CONSERVATION; GENETIC SCREENING; GENOME; GRAM NEGATIVE BACTERIUM; NONHUMAN; PREDICTION; PRIORITY JOURNAL; PROKARYOTE; PROTEIN ANALYSIS; PROTEIN FAMILY; SALMONELLA TYPHIMURIUM;

ACTINOBACTERIA (CLASS); BACTERIA (MICROORGANISMS); EUKARYOTA; FIRMICUTES; NEGIBACTERIA; PROKARYOTA; PROTEOBACTERIA; SALMONELLA TYPHIMURIUM; TYPHIMURIUM; UNCULTURED ACTINOMYCETE;

EID: 0035020714     PISSN: 13500872     EISSN: None     Source Type: Journal    
DOI: 10.1099/00221287-147-5-1137     Document Type: Article

References (44)

1. Andres, H. H., Kolb, H. J., Schreiber, R. J. & Weiss, L. (1983). Characterisation of the active site, substrate specificity and kinetic properties of acetyl-CoA: arylamine N-acetyltransferase from pigeon liver. Biochim Biophys Acta 746, 193-201.
2. Blum, M., Grant, D. M., McBride, W., Heim, M. & Meyer, U. A. (1990). Human arylamine N-acetyltransferase genes: isolation, chromosomal localization, and functional expression. DNA Cell Biol 9, 193-203.
3. Blum, M., Demierre, A., Grant, D. M., Heim, M. & Meyer, U. A. (1992). Molecular mechanism of slow acetylation of drugs and carcinogens in humans. Proc Natl Acad Sci U S A 88, 5237-5241.
4. Chang, F. C. & Chung, J. G. (1998). Evidence for arylamine N-acetyltransferase activity in the Escherichia coli. Curr Microbiol 36, 125-130.
5. Cole, S. T., Brosch, R., Parkhill, J. & 39 other authors (1998). Deciphering the biology of Mycobacterium tuberculosis from the complete genome sequence. Nature 393, 537-544.
6. Cribb, A. E., Grant, D. M., Miller, M. A. & Spielberg, S. P. (1991). Expression of monomorphic arylamine N-acetyltransferase (NAT1) in human leukocytes. J Pharmacol Exp Ther 259, 1241-1246.
7. Deguchi, T., Mashimoto, M. & Suzuki, T. (1990). Correlation between acetylator phenotypes and genotypes of polymorphic arylamine N-acetyltransferase in human liver. J Biol Chem 265, 12757-12760.
8. Delomenie, C., Goodfellow, G. H., Krishnamoorthy, R., Grant, D. M. & Dupret, J. M. (1997). Study of the role of the highly conserved residues Arg(9) and Arg(64) in the catalytic function of human N-acetyltransferases NAT1 and NAT2 by site-directed mutagenesis. Biochem J 323, 207-215.
9. Ellard, G. A. & Gammon, P. T. (1976). Pharmacokinetics of isoniazid metabolism in man. Biopharm 4, 83-113.
10. Engel, C. & Wierenga, R. (1996). The diverse world of coenzyme A binding proteins. Curr Opin Struct Biol 6, 790-797.
11. Evans, D. A. P., Manley, K. A. & McKuisick, V. A. (1960). Genetic control of isoniazid acetylation in man. Br Med J 2, 485-491.
12. Floss, H. & Yu, T.-W. (1999). Lessons from the rifamycin biosynthetic gene cluster. Curr Opin Chem Biol 3, 592-597.
13. French, C., Rosser, S., Davies, G., Nicklin, S. & Bruce, N. (1999). Biodegradation of explosives by transgenic plants expressing pentaerythritol and tetranitrate reductase. Nat Biotechnol 17, 491-494.
14. Fulco, A. (1991). P450BM-3 and other inducible P450 cytochromes: biochemistry and regulation. Annu Rev Pharmacol Toxicol 31, 177-203.
15. Hanna, P. (1996). Metabolic activation and detoxification of arylamines. Curr Med Chem 3, 195-210.
16. Hein, D., Grant, D. & Sim, E. (2000). Update on consensus arylamine N-acetyltransferase gene nomenclature. Pharmacogenetics 10, 1-2.
17. Hickman, D., Palamanda, J., Unadkat, J. & Sim, E. (1995). Enzyme kinetic properties of human recombinant arylamine N-acetyltransferase 2 allotypic variants expressed in E. coli. Biochem Pharmacol 50, 697-703.
18. Hinds, J., Mahenthiralingham, E., Kempsell, K., Duncan, K., Stokes, R., Parish, T. & Stoker, N. (1999). Enhanced gene replacement in mycobacteria. Microbiology 145, 519-527.
19. Hubbard, T., Tramontano, A. & Team, I. W. (1996). Update on protein structure prediction: results of the 1995 IRBM workshop. Folding Design 1, R55-R63.
20. King, C. M., Land, S. J., Jones, R. F., Debiec-Rychter, M., Lee, M. S. & Wang, C. Y. (1997). Role of acetyltransferases in the metabolism and carcinogenicity of aromatic amines. Mutat Res 12, 123-128.
21. Kinoshita, K., Sadanami, K., Kidera, A. & Go, N. (1999). Structural motif of phosphate-binding site common to various protein superfamilies: all-against-all structural comparison of protein-mononucleotide complexes. Protein Eng 12, 11-14.
22. Kunst, F., Ogasawara, N., Moszer, I. & 148 other authors (1997). The complete genome sequence of the gram-positive bacterium Bacillus subtilis. Nature 390, 249-256.
23. McCoy, E., Anders, M. & Rosenkranz, H. (1983). The basis of the insensitivity of Salmonella typhimurium strain TA98/1,8-DNP6 to the mutagenic action of nitroarenes. Mutat Res 121, 17-23.
24. Minchin, R. F. (1995). Acetylation of para-aminobenzoyl-glutamate, a folate catabolite, by recombinant human NAT and U937 cells. Biochem J 307, 1-3.
25. Ohsako, S. & Deguchi, T. (1990). Cloning and expression of cDNAs for polymorphic and monomorphic arylamine N-acetyltransferases of human liver. J Biol Chem 265, 4630-4634.
26. Parish, T. & Stoker, N. (1998). Mycobacterial Protocols. New Jersey: Humana.
27. Parish, T., Mahenthiralingam, E., Draper, P., Davis, E. O. & Colston, M. J. (1997). Regulation of the inducible amidase gene of Mycobacterium smegmatis. Microbiology 143, 2267-2276.
28. Payton, M. & Pinter, K. (1999). A rapid and novel method for the extraction of RNA from wild-type and genetically modified kanamycin-resistant mycobacteria. FEMS Microbiol Lett 180, 141-146.
29. Payton, M., Auty, R., Delgoda, R., Everett, M. & Sim, E. (1999). Cloning and characterisation of arylamine N-acetyltransferase genes of M. smegmatis and M. tuberculosis: increased expression results in isoniazid resistance. J Bacteriol 181, 1343-1347.
30. Poupin, P., Godon, J., Zumstein, E. & Truffaut, N. (1999). Degradation of morpholine, piperidine, and pyrolidine by mycobacteria: evidence for the involvement of cytochrome P450. Can J Microbiol 45, 209-216.
31. Risch, A., Wallace, D. M., Bathers, S. & Sim, E. (1995). Slow N-acetylation genotype is a susceptibility factor in occupational and smoking related bladder cancer. Hum Mol Genet 4, 231-236.
32. Sambrook, J., Fritsch, E. F. & Maniatis, T. (1989). Molecular Cloning: a Laboratory Manual, 2nd edn. Cold Spring Harbor, NY: Cold Spring Harbor Laboratory.
33. Schupp, T., Toupet, C., Engel, N. & Goff, S. (1998). Cloning and sequence analysis of the putative rifamycin polyketide synthase gene cluster from Amycolatopsis mediterranei. FEMS Microbiol Lett 159, 201-207.
34. Sim, E., Payton, M., Noble, M. & Minchin, R. (2000). An update on genetic, structural and functional studies of arylamine N-acetyltransferases in cucaryotes and procaryotes. Hum Mol Genet 9, 2435-2441.
35. Sinclair, J. & Sim, E. (1997). A fragment consisting of the first 204 amino-terminal amino acids of human arylamine N-acetyl transferase one (NAT1) and the first transacetylation step of catalysis. Biochem Pharmacol 53, 11-16.
36. Sinclair, J., Delgoda, R., Noble, M., Jarmin, S., Goh, N. & Sim, E. (1998). Purification, characterisation and crystallisation of an N-hydroxyarylamine O-acetyltransferase from Salmonella typhimurium. Protein Expr Purif 12, 371-380.
37. Sinclair, J., Sandy, J., Delgoda, R., Sim, E. & Noble, M. (2000). The crystal structure of arylamine N-acetyltransferase reveals a catalytic triad. Nat Struct Biol 7, 560-564.
38. Sohng, J.-K., Oh, T.-J., Lee, J.-J. & Kim, C.-G. (1997). Identification of a gene cluster of biosynthetic genes of rubradirin substructures in S. achromogenes var. rubradis NRRL3061. Mol Cell 7, 674-681.
39. Tang, L., Yoon, Y., Choi, C.-Y. & Hutchinson, C. (1998). Characterisation of the enzymatic domains in the modular polyketide synthase involved in rifamycin B biosynthesis by Amycolatopsis mediterranei. Gene 216, 255-265.
40. Vatsis, K. P., Weber, W. W., Bell, D. A. & 10 other authors (1995). Nomenclature for N-acetyltransferases. Pharmacogenetics 5, 1-17.
41. Ward, A., Summers, M. & Sim, E. (1995). Purification of recombinant human NAT1 expressed in E. coli. Biochem Pharmacol 49, 1759-1767.
42. Watanabe, M., Sofuni, T. & Nohmi, T. (1992). Involvement of Cys69 residue in the catalytic mechanism of N-hydroxyarylamine O-acetyltransferase of Salmonella typhimurium. Sequence similarity at the amino acid level suggests a common catalytic mechanism of acetyltransferase for S. typhimurium and higher organisms. J Biol Chem 267, 8429-8436.
43. Weber, W. W. & Hein, D.W. (1985). Arylamine N-acetyltransferases. Pharmacol Rev 37, 25-79.
44. Yu, T.-W., Shen, Y., Doi-Katayama, Y., Tang, L., Park, C., Moore, B., Hutchinson, C. & Floss, H. (1999). Direct evidence that the rifamycin polyketide synthase assembles polyketide chains processively. Proc Natl Acad Sci U S A 96, 9051-9056.