Inactivation of deacetoxycephalosporin C synthase in extracts of Streptomyces clavuligerus during bioconversion of penicillin G to deacetoxycephalosporin G

Enzyme and Microbial Technology

Volumn 25, Issue 6, 1999, Pages 497-501

  Adrio, José L ^a   Cho, Hiroshi ^a   Piret, Jacqueline M ^b   Demain, Arnold L ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

^b NORTHEASTERN UNIVERSITY   (United States)

Author keywords

Bioconversion; Cephalosporins; Deacetoxycephalosporin G; Penicillin G; Streptomyces clavuligerus

Indexed keywords

ANTIBIOTICS; BACTERIA; BIOCONVERSION; CATALYST DEACTIVATION; COMPOSITION EFFECTS; SUBSTRATES;

DEACETOXYCEPHALOSPORIN; PENICILLIN;

ENZYMES;

2 OXOGLUTARIC ACID; ASCORBIC ACID; CATALASE; DEACETOXYCEPHALOSPORIN C; DIMETHYL SULFOXIDE; DITHIOTHREITOL; FERROUS ION; HYDROGEN PEROXIDE; MANNITOL; MERCAPTOETHANOL; PENICILLIN G; SYNTHETASE;

ARTICLE; BIOTRANSFORMATION; CHEMICAL REACTION KINETICS; ENZYME INACTIVATION; ENZYME SPECIFICITY; NONHUMAN; REACTION ANALYSIS; STREPTOMYCES CLAVULIGERUS;

STREPTOMYCES CLAVULIGERUS;

EID: 0033199459     PISSN: 01410229     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0141-0229(99)00084-8     Document Type: Article

References (23)

1. Kohsaka M., Demain A.L. Conversion of penicillin N to cephalosporin(s) by cell-free extracts of Cephalosporium acremonium. Biochem Biophys Res Commun. 70:1976;465-473.
2. Yoshida M., Konomi T., Kohsaka M., Baldwin J.E., Hershen S., Singh P., Hunt N.A., Demain A.L. Cell-free ring expansion of penicillin N to deacetoxycephalosporin C by Cephalosporium acremonium CW-19 and its mutants. Proc Natl Acad Sci USA. 75:1978;6253-6257.
3. Jensen S.E., Westlake D.W.S., Bowers R.J., Wolfe S. Cephalosporin production by cell free extracts from Streptomyces clavuligerus. J Antibiot. 35:1982;1351-1360.
4. Kupka J., Shen Y.Q., Wolfe S., Demain A.L. Partial purification and properties of the α-ketoglutarate-linked ring expansion enzyme of β-lactam biosynthesis of Cephalosporium acremonium. FEMS Microbiol Lett. 16:1983;1-6.
5. Dotzlaf J.E., Yeh W.K. Purification and properties of deacetoxycephalosporin C synthetase from recombinant Escherichia coli and its comparison with the native enzyme purified from Streptomyces clavuligeruis. J Biol Chem. 264:1989;10219-10227.
6. Abbott M., Udenfriend S. α-Ketoglutarate-coupled dioxygenases. Hayaishi O. Molecular mechanisms of oxygen activation. 1974;167-214 Academic Press, New York.
7. Shen Y.Q., Wolfe S., Demain A.L. Desacetoxycephalosporin C synthetase importance of order of cofactor/reactant addition . Enzyme Microb Technol. 6:1984;402-404.
8. Yeh W.K., Dotzlaf J.E., Huffman G.W. Biochemical characterization and evolutionary implication of β-lactam expandase/hydroxylase, expandase and hydroxylase. Kleinkauf H., von Doehren H. 50 years of penicillin history and trends . 1994;208-223 Public, Prague.
9. Maeda K., Luengo J.M., Ferrero O., Wolfe S., Lebedev M.Y., Fang A., Demain A.L. The substrate specificity of deacetoxycephalosporin C synthetase ("expandase") of Streptomyces clavuligerus is extremely narrow. Enzyme Microb Technol. 17:1995;231-234.
10. Dotzlaf J.E., Yeh W.K. Copurification and characterization of deacetoxycephalosporin C synthetase/hydroxylase from Cephalosporium acremonium. J Bacteriol. 169:1987;1611-1618.
11. Baldwin J.E., Adlington R.N., Coates J.B., Crabbe J.C., Keeping J.W., Knight G.C., Nomoto J., Scholfield C.J., Ting H.H. Enzymatic ring expansion of penicillins to cephalosporins side chain specificity . J Chem Soc Chem Commun. 1987;374-375.
12. Cho H., Adrio J.L., Luengo J.M., Wolfe S., Ocran S., Hintermann G., Piret J., Demain A.L. Elucidation of conditions allowing conversion of penicillin G and other biosynthetic penicillins to deacetoxycephalosporins by resting cells and extracts of Streptomyces clavuligerus NP1. Proc Natl Acad Sci USA. 95:1998;11544-11548.
13. Baldwin JE, Morgan N, Sutherland JD. Genetic engineering of cephalosporin biosynthesis. In: Léger N, editor. Abstracts 7th International Symposium on the Genetics of Industrial Microorganisms (GIM). Montreal, Canada. National Research Council, Ottawa, Canada 1994. p. 184, 262.
14. 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.
15. Yu H., Serpe E., Romero J., Coque J.-J., Maeda K., Oelgeschlager M., Hintermann G., Liras P., Martin J.-F., Demain A.L., Piret J. Possible involvement of the lysine e-aminotransferase gene (lat) in the expression of the genes encoding ACV synthetase (pcbAB) and isopenicillin N synthase (pcbC) in Streptomyces clavuligerus. Microbiology. 140:1994;3367-3377.
16. Fucci L., Oliver C.N., Coon M.J., Stadtman E.R. Inactivation of key enzymes by mixed-function oxidation reactions possible implication in protein turnover and ageing . Proc Natl Acad Sci USA. 80:1983;1521-1525.
17. Nakamura S. Initiation of sulfite oxidation by spinach ferredoxin-NADP reductase and ferredoxin system a model experiment of the superoxide anion radical production by metalloflavoproteins . Biochem Biophys Res Commun. 41:1970;177-183.
18. Levine R.L., Oliver C.N., Fulks R.H., Stadtman E.R. Turnover of bacterial glutamine synthetase oxidative inactivation precedes proteolysis . Proc Natl Acad Sci USA. 78:1981;2120-2124.
19. Lübbe C., Wolfe S., Demain A.L. Dithiothreitol reactivates desacetoxycephalosporin C synthetase after inactivation. Enzyme Microb Technol. 7:1985;353-356.
20. Popenoe E.A., Aronson R.B., Van Slyke D.D. The sulfhydryl nature of collagen proline hydroxylase. Arch Biochem Biophys. 133:1969;286-292.
21. Rhoads R.E., Udenfriend S. Purification and properties of collagen proline hydroxylase from newborn rat skin. Arch Biochem Biophys. 139:1970;329-339.
22. Golan-Goldhirsh A., Osuga D.T., Chen A.O., Whitaker J.R. Effect of ascorbic acid and copper on proteins. D'Souza V.T., Feder J. The bioorganic chemistry of enzymatic catalysis an homage to Myron L. Bender . 1992;61-76 CRC Press, Boca Raton, FL.
23. Valegard K., van Scheltinga A.C.T., Lloyd M.D., Hara T., Ramaswamy S., Perrakis A., Thompson A., Lee H.-J., Baldwin J.E., Schofield C.J., Hajdu J., Andersson I. Structure of a cephalosporin synthase. Nature (London). 394:1998;805-809.