Construction of hybrid bacterial deacetoxycephalosporin C synthases (expandases) by in vivo homeologous recombination

Enzyme and Microbial Technology

Volumn 31, Issue 7, 2002, Pages 932-940

  Adrio, Jose L ^a,b,c   Hintermann, Gilberto A ^a   Demain, Arnold L ^b   Piret, Jacqueline M ^a  

^a NORTHEASTERN UNIVERSITY   (United States)

^b MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

^c Puleva Biotech SA   (Spain)

Author keywords

Deacetoxycephalosporin C synthase; Expandase; Hybrid enzymes; Nocardia lactamdurans; Streptomyces clavuligerus

Indexed keywords

BACTERIA; BIOASSAY; DNA SEQUENCES; ENZYMES;

HOMEOLOGOUS RECOMBINATION;

BIOTECHNOLOGY;

ADICILLIN; DEACETOXYCEPHALOSPORIN C SYNTHASE; HYBRID PROTEIN; PENICILLIN G; SYNTHETASE; UNCLASSIFIED DRUG;

AMINO TERMINAL SEQUENCE; ARTICLE; BACTERIAL STRAIN; BACTERIUM COLONY; BIOASSAY; CARBOXY TERMINAL SEQUENCE; CONTROLLED STUDY; DNA SEQUENCE; ENZYME ACTIVITY; ENZYME PURIFICATION; ESCHERICHIA COLI; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HOMOLOGOUS RECOMBINATION; NOCARDIA; NONHUMAN; NUCLEOTIDE SEQUENCE; SPECIES DIFFERENCE; STREPTOMYCES CLAVULIGERUS;

ESCHERICHIA COLI; NOCARDIA LACTAMDURANS; STREPTOMYCES CLAVULIGERUS;

EID: 0037010875     PISSN: 01410229     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0141-0229(02)00179-5     Document Type: Article

References (32)

1. Kohsaka M., Demain A.L. Conversion of penicillin N to deacetoxycephalosporin(s) by cell free extracts of Cephalosporium acremonium. Biochem. Biophys. Res. Commun. 70:1976;465-473.
2. Valegard K., van Scheltinga A.C., Lloyd M.D., Hara T., Ramaswamy S., Perrakis A.et al. Structure of a cephalosporin synthase. Nature. 394:1998;805-809.
3. Lloyd M.D., Lee H.J., Harlos K., Zhang Z.H., Baldwin J.E., Schofield C.J.et al. Studies on the active site of deacetoxycephalosporin C synthase. J. Mol. Biol. 287:1999;943-960.
4. Lee H.J., Lloyd M.D., Harlos K., Schofield C.J. The effect of cysteine mutations on recombinant deacetoxycephalosporin C synthase from S. clavuligerus. Biochem. Biophys. Res. Commun. 267:2000;445-448.
5. Sim J., Sim T.S. Mutational evidence supporting the involvement of tripartite residues His183, Asp185, and His243 in Streptomyces clavuligerus deacetoxycephalosporin C synthase for catalysis. Biosci. Biotechnol. Biochem. 64:2000;828-832.
6. Chin H.S., Sim J., Sim T.S. Mutation of N304 to leucine in Streptomyces clavuligerus deacetoxycephalosporin C synthase creates an enzyme with increased penicillin analogue conversion. Biochem. Biophys. Res. Commun. 287:2001;507-513.
7. Lee H.J., Lloyd M.D., Clifton I.J., Harlos K., Dubus A., Baldwin J.E.et al. Alteration of the co-substrate selectivity of deacetoxycephalosporin C synthase. The role of arginine 258. J. Biol. Chem. 276:2001;18290-18295.
8. Dubus A., Lloyd M.D., Lee H.J., Schofield C.J., Baldwin J.E., Frere J.M. Probing the penicillin sidechain selectivity of recombinant deacetoxycephalosporin C synthase. Cell Mol. Life Sci. 58:2001;835-843.
9. Cho H., Adrio J.L., Luengo J.M., Wolfe S., Ocran S., Hintermann G.et al. Elucidation of conditions allowing conversion of penicillin G and other penicillins to deacetoxycephalosporins by resting cells and extracts of Streptomyces clavuligerus. Proc. Natl. Acad. Sci. U.S.A. 95:1998;11544-11548.
10. Baez-Vasquez M.A., Adrio J.L., Piret J.M., Demain A.L. Further studies on the bioconversion of penicillin G into deacetoxycephalosporin G by resting cells of Streptomyces clavuligerus NP1. Appl. Biochem. Biotechnol. 81:1999;145-152.
11. Crawford L., Stepan A.M., McAda P.C., Rambosek J.A., Conder M.J., Vinci V.A.et al. Production of cephalosporin intermediates by feeding adipic acid to recombinant Penicillium chrysogenum strains expressing ring expansion activity. Biotechnology. 13:1995;58-62.
12. Adrio J.L., Cho H., Piret J.M., Demain A.L. Inactivation of deacetoxycephalosporin C synthase during conversion of penicillin G to deacetoxycephalosporin G by crude extracts of Streptomyces clavuligerus. Enzyme Microb. Technol. 25:1999;497-501.
13. Stemmer W.P.C. DNA Shuffling by random fragmentation and reassembly: in vitro recombination for molecular evolution. Proc. Natl. Acad. Sci. U.S.A. 91:1994;10747-10751.
14. Baltz R.H., Matsushima P. Advances in protoplast fusion and transformation in Streptomyces. Experientia. 46:1983;143-148.
15. Weber H., Weissmann C. Formation of genes coding for hybrid proteins by recombination between related, cloned genes in E. coli. Nucl. Acids Res. 11:1983;5661-5669.
16. Conrad B., Hoang V., Hofmeister J. Hybrid Bacillus amyloliquefaciens alpha-amylases. Construction, properties and sequence determinants. Eur. J. Biochem. 230:1995;481-490.
17. Beguin P. Hybrid enzymes. Curr. Opin. Biotechnol. 10:1999;336-340.
18. Lomovskaya N.D., Voeykova T.A., Mkrtumian N.M. Construction and properties of hybrids obtained in interspecies crosses between Streptomyces coelicolor A3(2) and Streptomyces griseus Kr 15. J. Gen. Microbiol. 98:1977;187-198.
19. Mazieres N., Peyre M., Penasse L. Interspecific recombination among aminoglycoside producing streptomycetes. J. Antibiot. 34:1981;544-550.
20. Gomi S., Ikeda D., Nakamura H., Naganawa H., Yamashita F., Hotta K.et al. Isolation and structure of a new antibiotic indolizomycin produced by a strain SK2-52 obtained by interspecies fusion treatment. J. Antibiot. 37:1984;1491-1494.
21. Hosted T.J., Baltz R.H. Mutants of Streptomyces roseosporus that express enhanced recombination within partially homeologous genes. Microbiology. 142:1996;2803-2813.
22. Smith G.R. Homeologous recombination in prokaryotes. Microbiol. Rev. 54:1988;1-36.
23. Perry JJ, Staley JT. Genetic exchange. In: Microbiology: Dynamics and Diversity. New York: Saunders, 1997. p. 346-66.
24. Coque J.J.R., MarÌn J.F., Liras P. Characterization and expression in Streptomyces lividans of cefD and cefE genes from Nocardia lactamdurans: the organization of the cephamycin cluster differs from that in Streptomyces clavuligerus. Mol. Gen. Genet. 236:1993;453-458.
25. Palmer B.R., Marinus M.G. The dam and dcm strains of Escherichia coli: a review. Gene. 143:1994;1-12.
26. Hopwood DA, Bibb MJ, Chater KF, Kieser T, Bruton CI, Kieser HM, et al. Genetic Manipulation of Streptomyces: A Laboratory Manual. Norwich: John Innes Foundation, 1985.
27. Mahro B., Demain A.L. In vivo conversion of penicillin N into a cephalosporin type antibiotic by a non-producing mutant of Streptomyces clavuligerus. Appl. Microbiol. Biotechnol. 27:1987;272-275.
28. Sambrook J, Fritsch EF, Maniatis T. Molecular Cloning: A Laboratory Manual. Cold Spring Harbor, NY: Cold Spring Harbor Laboratory Press, 1989.
29. Hintermann G. Aspects of the Genomic Organization in Streptomyces glaucescens. Thesis, Swiss Federal Institute of Technology (ETH), Zurich, 1984.
30. Hopwood D.A., Bibb M.J., Chater K.F., Kieser T. Plasmids and phage vectors for gene cloning and analysis in Streptomyces. Meth. Enzymol. 153:1987;116-167.
31. Shen Y.Q., Wolfe S., Demain A.L. Deacetoxycephalosporin C synthetase: importance of order of cofactor/reactant addition. Enzyme Microbiol. Technol. 6:1984;402-404.
32. Fernandez M.J., Adrio J.L., Piret J.M., Wolfe S., Ro S., Demain A.L. Stimulatory effect of growth in the presence of alcohols on biotransformation of penicillin G into cephalosporin-type antibiotics by resting cells of Streptomyces clavuligerus NP1. Appl. Microbiol. Biotechnol. 52:1999;484-488.