Potent inhibition of macrophomate synthase by reaction intermediate analogs

Bioscience, Biotechnology and Biochemistry

Volumn 64, Issue 11, 2000, Pages 2368-2379

  Oikawa, Hideaki ^a   Yagi, Kenji ^a   Ohashi, Satoshi ^a   Watanabe, Kenji ^a   Mie, Takashi ^a   Ichihara, Akitami ^a   Honma, Mamoru ^a   Kobayashi, Kimiko ^a,b  

^a HOKKAIDO UNIVERSITY   (Japan)

^b INST OF PHYS AND CHEMICAL RESEARCH   (Japan)

Author keywords

2 pyrone; Inhibitors; Macrophomate synthase; Oxalacetate

Indexed keywords

ENZYME INHIBITOR; MACROPHOMATE SYNTHASE; MULTIENZYME COMPLEX; OXALOACETIC ACID DERIVATIVE; PYRONE DERIVATIVE;

ARTICLE; BINDING COMPETITION; CHEMISTRY; DRUG ANTAGONISM; ENZYME SPECIFICITY; METABOLISM; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

BINDING, COMPETITIVE; ENZYME INHIBITORS; MULTIENZYME COMPLEXES; OXALOACETIC ACIDS; PYRONES; STRUCTURE-ACTIVITY RELATIONSHIP; SUBSTRATE SPECIFICITY;

EID: 0034329716     PISSN: 09168451     EISSN: 13476947     Source Type: Journal    
DOI: 10.1271/bbb.64.2368     Document Type: Article

References (18)

1. Oikawa, H., Watanabe, K., Yagi, K., Ohashi, S., Mie, T., Ichihara, A., and Honma, M., Macropho-mate synthase: Unusual enzyme catalyzing multiple reactions from pyrones to benzoates. Tetrahedron Lett., 40, 6983-6986 (1999).
2. Watanabe, K., Oikawa, H., Yagi, K., Ohashi, S., Mie, T., Ichihara, A., and Honma, M., Macropho-mate synthase: Characterization, sequence, and expression in Escherichia coli of the novel enzyme catalyzing unusual multistep transformation from 2-pyrones to benzoates. J. Biochem., 127, 465-471 (2000).
3. Sakurai, I., Suzuki, H., Shimizu, S., and Yamamoto, Y., Novel biotransformation of a 2-pyrone to a substituted benzoic acid. Chem. Pharm. Bull., 33, 5141-5143 (1985).
4. Sakurai, I., Shimizu, S., and Yamamoto, Y., Studies on metabolites of Macrophoma commeliae. III. Chem. Pharm. Bull., 36, 1328-1335 (1988).
5. Sakurai, I., Miyajima, H., Akiyama, K., Shimizu, S., and Yamamoto, Y., Studies on metabolites of Macrophoma commeliae. IV. Chem. Pharm. Bull., 36, 2003-2011 (1988).
6. Watanabe, K., Mie, T., Ichihara, A., Oikawa, H., and Honma, M., Detailed Reaction Mechanism of Macrophomate Synthase: Extraordinary Enzyme Catalyzing Five-step Transformation from 2-Pyrones to Benzoates. J. Biol. Chem., in press.
7. Widlanski, T. S., Bender, S. L., and Knowles, J. R., Dehydroquinate synthase: The use of substrate analogues to probe the late steps of the catalyzed reaction. Biochemistry, 28, 7572-7582 (1989).
8. Kudo, F., Hosomi, Y., Tamegai, H., and Kakinuma, K., Purification and characterization of 2-deoxy-scyl-lo-inosose synthase derived from Bacillus circulans. A crucial carbocyclization enzyme in the biosynthesis of 2-deoxystreptamine-containing aminoglycoside antibiotics. J. Antibiot., 52, 81-88 (1999).
9. Kudo, F., Tamegai, H., Fujiwara, T., Tagami, U., Hirayama, K., and Kakinuma, K., Molecular cloning of the gene for the key carbocycle-forming enzyme in the biosynthesis of 2-deoxystreptamine-containing aminocyclitol antibiotics and its comparison with dehydroquinate synthase. J. Antibiot., 52, 559-571 (1999).
10. Watanabe, K., Mie, T., Ichihara, A., Oikawa, H., and Honma, M., Substrate diversity of macropho-mate synthase catalyzing unusual multistep transformation from 2-pyrones to benzoates. Biosci. Biotechnol. Biochem., 64, 530-538 (2000).
11. Watanabe, K., Mie, T., Ichihara, A., Oikawa, H., and Honma, M., Reaction mechanism of the macro-phomate synthase: Experimental evidence on intermediacy of a bicyclic compound. Tetrahedron Lett., 41, 1443-1446 (2000).
12. Oikawa, H., Yagi, K., Watanabe, K., Honma, M., and Ichihara, A., Biosynthesis of macrophomic acid: Plausible involvement of intermolecular Diels-Alder reaction. J. Chem. Soc., Chem. Commun., 97-98 (1997).
13. Chao, H. S.-I. and Berchtold, G. A., Inhibition of chorismate mutase activity of chorismate mutase-prephenate dehydrogenase from Aerobacter aer-ogenes. Biochemistry, 21, 2778-2781 (1982).
14. White, K. B. and Reusch, W., The synthesis of bicyclo[2.2.2]octan-2-ones by sequential Michael reactions. Tetrahedron, 34, 2439-2443 (1978).
15. Paquette, L. A. and Poupart, M.-A., Studies directed toward the total synthesis of cerorubenic acid-III. J. Org. Chem., 58, 4245-4253 (1993).
16. Okamura, H., Iwagawa, T., and Nakatani, M., A base catalyzed Diels-Alder reaction of 3-hydroxy-2-pyrone. Tetrahedron Lett., 36, 5939-5942 (1995).
17. Bartlett, P. A. and Myerson, J., Stereoselective epoxidation of acyclic olefmic carboxylic acids via iodolactonization. J. Am. Chem. Soc., 100, 3950-3952 (1978).
18. Hoye, T. R. and Koltun, D. O., An NMR strategy for determination of configuration of remote stereogenic centers—3-Methylcarboxylic acids. J. Am. Chem. Soc., 120, 4638-4643 (1998).