- 1) Widlanski, T. S., Bender, S. L., and Knowles, J. R., Dehydroquinate synthase. J. Am. Chem. Soc., 109, 1873-1875 (1987).
- 2) Widlanski, T. S., Bender, S. L., and Knowles, J. R., Dehydroquinate synthase: a sheep in wolf’s clothing? J. Am. Chem. Soc., 111, 2299-2300 (1989).
- 3) Iwase, N., Kudo, F., Yamauchi, N., and Kakinuma, K., Substrate specificity of 2-deoxy-scyllo-inosose synthase, the starter enzyme for 2-deoxystreptamine biosynthesis, toward deoxyglucose-6-phosphates and proposed mechanism. Biosci. Biotechnol. Biochem., 62, 2396-407 (1998).
- 4) 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).
- 5) Sakurai, I., Miyajima, H., Akiyama, K., Shimizu, S., and Yamamoto, Y., Studies on metabolites of Macrophoma commelinae. IV. Chem. Pharm. Bull., 36, 2003-2011 (1988).
- 6) Sakurai, I., Shimizu, S., and Yamamoto, Y., Studies on metabolites of Macrophoma commelinae. III. Chem. Pharm. Bull., 36, 1328-1335 (1988).
- 7) Sato, H., Konoma, K., and Sakamura, S., The structure of pyrenochaetic acids. Agric. Biol. Chem., 45, 1675-1679 (1981).
- 8) Sato, H., Konoma, K., and Sakamura, S., The structure of pyrenocines. Agric. Biol. Chem., 43, 2409-2411 (1979).
- 9) Sato, H., Konoma, K., Sakamura, S., Furusaki, A., Matsumoto, T., and Matsuzaki, T., Revision of structure of pyrenocine A. Agric. Biol. Chem., 45, 795-797 (1981).
- 10) 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).
- 11) Oikawa, H., Watanabe, K., Yagi, K., Ohashi, S., Mie, T., Ichihara, A., and Honma, M., Macrophomate synthase: unusual enzyme catalyzing multiple reactions from pyrones to benzoates. Tetrahedron Lett., 40, 6983-6986 (1999).
- 12) Watanabe, K., Oikawa, H., Yagi, K., Ohashi, S., Mie, T., Ichihara, A., and Honma, M., Macrophomate synthase: characterization, sequence, and expression in Escherichia coli of the novel enzyme catalyzing unusual multistep transformation from 2-pyrones to benzoates. J. Biochem., in press.
- 13) Holenstein, J. E., Kern, H., Stoessl, A., and Stothers, J. B., The marticins: evidence for a mixed origin from the polyketide and tricarboxylic acid pathways by [2-13C1] and [1, 2-13C2]-acetate incorporation experiments. Tetrahedron Lett., 24, 4059-4062 (1983).
- 14) Nakajima, H., Toratsu, Y., Fujii, Y., Ichinoe, M., and Hamasaki, T., Biosynthesis of sorkinianin. Tetrahedron Lett., 39, 1013-1016 (1998).
- 15) Kimura, Y., Fujioka, H., Hamasaki, T., Furihata, K., and Fujioka, S., Botryslactone, a new plant growth regulator produced by Botrytis Squamosa. Tetrahedron Lett., 36, 7673-7676 (1995).
- 16) Chesters, N. C. J. E. and O’Hagan, D., Biosynthesis of the fungal metabolite, piliformic acid (2-hexylidene-3-methylsuccinic acid). J. Chem. Soc., Perkin Trans. 1, 827-834 (1997).
- 17) Butt, M. A. and Elvidge, J. A., Heterocyclic syntheses with malonyl chloride. Part III. Hydroxypyrones from 1,3-diketones. J. Chem. Soc., 4483-4489 (1963).
- 18) Ichihara, A., Murakami, K., and Sakamura, S., Synthesis of pyrenocines A, B and pyrenochaetic acid A. Tetrahedron, 43, 5245-5250 (1987).
- 19) Oikawa, H., Kobayashi, T., Katayama, K., Suzuki, Y., and Ichihara, A., Total synthesis of (-)-solanapyrone A via enzymatic Diels-Alder reaction of prosolanapyrone. J. Org. Chem., 63, 8748-8756 (1998).
- 20) Shimizu, S., Sakurai, I., and Yamamoto, Y., Isolation and structure of macommelins, novel metabolites of Macrophoma commelinae. Chem. Pharm. Bull., 31, 3781-3784 (1983).
- 21) Isaacs, N. S. and Kirkpatrick, D., The reactions of triphenylphosphine in carbon tetrachloride with enolisable ketones. J. Chem. Soc., Chem. Commun., 443-444 (1972).
- 22) Yamada, K., Infrared and ultraviolet spectra of α- and γ-pyrones. Bull. Chem. Soc. Jpn., 35, 1323-1329 (1962).
- 23) de March, P., Moreno-Mañas, M., and Ripoll, I., Functionalization of 4-hydroxy-6-methyl-2-pyrone at C-5 through [2, 3] sigmatropic rearrangements of allylic sulphonium ylides. Synth. Commun., 14, 521-531 (1984).
- 24) Harris, T. M., Harris, C. M., and Brush, C. K., Bromination of dehydroacetic acid. J. Org. Chem., 35, 1329-1333 (1970).
- 25) Wiley, R. H. and Smith, N. R., The condensation of ethyl acetoacetate to isodehydroacetic acid and ethyl ester. J. Am. Chem. Soc., 73, 3531-3533 (1951).
- 26) Dess, D. B. and Martin, J. C., Readily accessible 12-I-51 oxidant for the conversion of primary and secondary alcohols to aldehydes and ketones. J. Org. Chem., 48, 4155-4156 (1983).
- 27) Ireland, R. E. and Liu, L., An improved procedure for the preparation of the Dess-Martin periodinane. J. Org. Chem., 58, 2899 (1993).
Full access
Substrate Diversity of Macrophomate Synthase Catalyzing an Unusual Multistep Transformation from 2-Pyrones to Benzoates
Reprints and Corporate Permissions
Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?
To request a reprint or corporate permissions for this article, please click on the relevant link below:
Academic Permissions
Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?
Obtain permissions instantly via Rightslink by clicking on the button below:
If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.
Related research
People also read lists articles that other readers of this article have read.
Recommended articles lists articles that we recommend and is powered by our AI driven recommendation engine.
Cited by lists all citing articles based on Crossref citations.
Articles with the Crossref icon will open in a new tab.