Genes specific for the biosynthesis of clavam metabolites antipodal to clavulanic acid are clustered with the gene for clavaminate synthase 1 in Streptomyces clavuligerus

Antimicrobial Agents and Chemotherapy

Volumn 43, Issue 5, 1999, Pages 1215-1224

  Mosher, Roy H ^a,c   Paradkar, Ashish S ^a,d   Anders, Cecilia ^a   Barton, Barry ^b   Jensen, Susan E ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

^b GLAXOSMITHKLINE   (United Kingdom)

^c UNIVERSITY OF ILLINOIS AT SPRINGFIELD   (United States)

^d DIVERSA CORPORATION   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CEPHAMYCIN C; CLAVULANIC ACID; DRUG METABOLITE; SYNTHETASE;

AMINO ACID SEQUENCE; ARTICLE; DELETION MUTANT; DNA FLANKING REGION; DRUG STRUCTURE; DRUG SYNTHESIS; GENE CASSETTE; GENE CLUSTER; GENE DISRUPTION; GENE INSERTION; NONHUMAN; NUCLEOTIDE SEQUENCE; PRIORITY JOURNAL; REACTION ANALYSIS; SEQUENCE ANALYSIS; STREPTOMYCES CLAVULIGERUS;

EID: 0032931680     PISSN: 00664804     EISSN: None     Source Type: Journal    
DOI: 10.1128/aac.43.5.1215     Document Type: Article

References (40)

1. Aidoo, K. A., A. Wong, D. C. Alexander, R. A. R. Rittammer, and S. E. Jensen. 1994. Cloning, sequencing and disruption of a gene from Streptomyces clavuligerus involved in clavulanic acid biosynthesis. Gene 147:41-46.
2. Bachmann, B. O., R. Li, and C. A. Townsend. 1998. β-Lactam synthetase: a new biosynthetic enzyme. Proc. Natl. Acad. Sci. USA 95:9082-9086.
3. Barton, B. 1996. Unpublished data.
4. Denis, F., and R. Brzezinski. 1991. An improved aminoglycoside resistance gene cassette for use in gram-negative bacteria and Streptomyces. FEMS Microbiol. Lett. 81:261-264.
5. Devereux, J., P. Haeberli, and O. Smithies. 1988. A comprehensive set of sequence analysis programs for the VAX. Nucleic Acids Res. 12:387-395.
6. Doran, J. L., B. K. Leskiw, A. K. Petrich, D. W. S. Westlake, and S. E. Jensen. 1990. Production of Streptomyces clavuligerus isopenicillin N synthase in Escherichia coli using two-cistron expression systems. J. Ind. Microbiol. 5:197-206.
7. Doran, J. L., B. K. Leskiw, S. Aippersbach, and S. E. Jensen. 1990. Isolation and characterization of a beta-lactamase-inhibitory protein from Streptomyces clavuligerus and cloning and analysis of the corresponding gene. J. Bacteriol. 172:4909-4918.
8. Egan, L. A., R. W. Busby, D. Iwata-Reuyl, and C. A. Townsend. 1997. Probable role of clavaminic acid as the terminal intermediate in the common pathway to clavulanic acid and the antipodal clavam metabolites. J. Am. Chem. Soc. 119:2348-2355.
9. Elson, S. W., K. H. Baggaley, J. Gillett, S. Holland, N. H. Nicholson, J. T. Sime, and S. R. Woroniecki. 1987. Isolation of two novel intracellular β-lactams and a novel dioxygenase cyclising enzyme from Streptomyces clavuligerus. J. Chem. Soc. Chem. Commun. 1987:1736-1738.
10. Elson, S. W., K. H. Baggaley, J. Gillett, S. Holland, N. H. Nicholson, J. T. Sime, and S. R. Woroniecki. 1987. The roles of clavaminic acid and proclavaminic acid in clavulanic acid biosynthesis. J. Chem. Soc. Chem. Commun. 1987:1739-1740.
11. 2]glutamic acid. J. Antibiot. 35:81-86.
12. 11a. European Bioinformaties Institute. 18 March 1999, revision date. [Online.] Fasta 3 database searches, http://www.ebi.ac.uk/htbin/fasta.py?request. [28 January 1999, last date accessed.]
13. Hopwood, D. A., M. J. Bibb, K. F. Chater, T. Kieser, C. J. Bruton, H. M. Kieser, D. J. Lydiate, C. P. Smith, J. M. Ward, and H. Schrempf. 1985. Genetic manipulation of Streptomyces: a laboratory manual. The John Innes Foundation, Norwich, United Kingdom.
14. Iwata-Reuyl, D., and C. A. Townsend. 1992. Common origin of clavulanic acid and other clavam metabolites in Streptomyces. J. Am. Chem. Soc. 114: 2762-2763.
15. Jane, J. W., L. A. Egan, and C. A. Townsend. 1995. Purification and characterization of clavaminate synthase from Streptomyces antibioticus: a multifunctional enzyme of clavam biosynthesis. J. Biol. Chem. 270:5399-5404.
16. Jensen, S. E., and A. L. Demain. 1995. Beta-lactams, p. 239-268. in L. C. Vining and C. Stuttard (ed.), Genetics and biochemistry of antibiotic production. Butterworth-Heinemann, Toronto, Ontario, Canada.
17. Jensen, S. E., D. C. Alexander, A. S. Paradkar, and K. A. Aidoo. 1993. Extending the β-lactam biosynthetic gene cluster in Streptomyces clavuligerus, p. 169-176. In R. H. Baltz, G. D. Hegeman, and P. L. Skatrud (ed.), Industrial microorganisms: basic and applied molecular genetics. American Society for Microbiology, Washington, D.C.
18. Katz, E., C. J. Thompson, and D. A. Hopwood. 1983. Cloning and expression of the ryrosinase gene from Streptomyces antibioticus in Streptomyces lividans. J. Gen. Microbiol. 129:2703-2714.
19. King, H. D., J. Langhärig, and J. J. Sanglier. 1986. Clavamycins, new clavam antibiotics from two variants of Streptomyces hygroscopicus. I. Taxonomy of the producing organisms, fermentation, and biological activities. J. Antibiot. 39:510-515.
20. Marck, C. 1988. 'DNA Strider': a 'C' program for the fast analysis of DNA and protein sequences on the Apple Macintosh family of computers. Nucleic Acids Res. 16:1829-1836.
21. Marsh, E. N., M. D.-T. Chang, and C. A. Townsend. 1992. Two isozymes of clavaminate synthase central to clavulanic acid formation: cloning and sequencing of both genes from Streptomyces clavuligerus. Biochemistry 31: 12648-12657.
22. McNaughton, H. J., J. E. Thirkettle, Z. Zhang, C. J. Schofield, S. E. Jensen, B. Barton, and P. Greaves. 1998. Beta-lactam synthetase: implications for beta-lactamase evolution. J. Chem. Soc. Chem. Commun. 1998:2325-2326.
23. 21a. National Center for Biotechnology Information. 19 March 1999 revision date. [Online.] The National Center for Biotechnology Information, http:// www.ncbi.nih.gov/BLAST/. [28 January 1999, last date accessed.]
24. Nicholson, N. H., K. H. Baggaley, R. Cassels, M. Davison, S. W. Elson, M. Fulston, J. W. Tyler, and S. R. Woroniecki. 1994. Evidence that the immediate biosynthetic precursor of clavulanic acid is its N-aldehyde analogue. J. Chem. Soc, Chem. Commun. 1994:1281-1282.
25. Paradkar, A., and S. E. Jensen. 1995. Functional analysis of the gene encoding the clavaminate synthase 2 isoenzyme involved in clavulanic acid biosynthesis in Streptomyces clavuligerus. J. Bacteriol. 177:1307-1314.
26. Paradkar, A. S., S. E. Jensen, and R. H. Mosher. 1997. Comparative genetics and molecular biology of β-lactam biosynthesis, p. 241-277. In W. R. Strohl (ed.), Biotechnology of antibiotics, 2nd ed., revised and expanded. Marcel Dekker, Inc., New York, N.Y.
27. 2]-D,L-glycerate in clavulanic acid biosynthesis. J. Chem. Soc. Chem. Commun. 1997:225-226.
28. Pruess, D. L., and M. Kellett. 1983. Ro-22-5417, a new clavam antibiotic from Streptomyces clavuligerus. I. Discovery and biological activity. J. Antibiot. 36:208-212.
29. Reading, C., and M. Cole. 1977. Clavulanic acid: a beta-lactamase-inhibiting beta-lactam from Streptomyces clavuligerus. Antimicrob. Agents Chemother. 11:852-857.
30. Sambrook, J., E. F. Fritsch, and T. Maniatis. 1989. Molecular cloning: a laboratory manual, 2nd ed. Cold Spring Harbor Laboratory Press, Cold Spring Harbor, N.Y.
31. Sanger, F., S. Nicklen, and A. R. Coulson. 1977. DNA sequencing with chain-terminating inhibitors. Proc. Natl. Acad. Sci. USA 74:5463-5467.
32. Stahl, D. A., and R. Amann. 1991. Development and application of nucleic acid probes, p. 205-248. In E. Stackebrandt and M. Goodfellow (ed.), Nucleic acid techniques in bacterial systematics. John Wiley & Sons Ltd., Toronto, Ontario, Canada.
33. Thirkettle, J. E., J. E. Baldwin, J. Edwards, J. P. Griffin, and C. J. Schofield. 1997. The origin of the β-lactam carbons of clavulanic acid. J. Chem. Soc. Chem Commun. 1997:1025-1026.
34. Toney, M. D., E. Hohenester, S. W. Cowen, and J. N. Jansonius. 1993. Dialkylglycine decarboxylase structure: bifunctional active site and alkali metal sites. Science 261:756-759.
35. Uchiyama, H., and B. Weisblum. 1985. N-Methyl transferase of Streptomyces erythraeus that confers resistance to the macrolide-lincosamide-streptogramin B antibiotics: amino acid sequence and its homology to cognate R-factor enzymes from pathogenic bacilli and cocci. Gene 38:103-110.
36. Valentine, B. P., C. R. Bailey, A. Doherty, J. Morris, S. W. Elson, K. H. Baggaley, and N. H. Nicholson. 1993. Evidence that arginine is a later metabolic intermediate than ornithine in the biosynthesis of clavulanic acid by Streptomyces clavuligerus. J. Chem. Soc. Chem. Commun. 1993:1210-1211.
37. Ward, J. M., G. R. Janssen, T. Kieser, M. J. Bibb, M. J. Buttner, and M. J. Bibb. 1986. Construction and characterisation of a series of multi-copy promoter-probe plasmid vectors for Streptomyces using the aminoglycoside phosphotransferase gene from Tn5 as indicator. Mol. Gen. Genet. 203:468-478.
38. Ward, J. M., and J. E. Hodgson. 1993. The biosynthetic genes for clavulanic acid and cephamycin production occur as a 'super-cluster' in three Streptomyces. FEMS Microbiol. Lett. 119:239-242.
39. Wu, T.-K., R. W. Busby, T. A. Houston, D. B. McIlwaine, L. A. Egan, and C. A. Townsend. 1995. Identification, cloning, sequencing, and overexpression of the gene encoding proclavaminate amidino hydrolase and characterization of protein function in clavulanic acid biosynthesis. J. Bacteriol. 177: 3714-3720.
40. Zoller, M. J., and M. Smith. 1987. Oligonucleotide-directed mutagenesis: a simple method using two oligonucleotide primers and a single-stranded DNA template. Methods Enzymol. 154:329-350.