A highly reactive and catalytically active model system for intradiol-cleaving catechol dioxygenases: Structure and reactivity of iron(III) catecholate complexes of N,N′-dimethyl-2,11-diaza3.31(2,6)pyridinophane

Angewandte Chemie (International Edition in English)

Volumn 34, Issue 23, 1996, Pages 2671-2674

  Koch, Welf O ^a   Krüger, Hans Jörg ^a  

^a Inst F Anorganische Angew C   (Germany)

Author keywords

Catechol dioxygenases; Enzyme catalysis; Iron compounds; Oxygenations

Indexed keywords

EID: 33748238499     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (21)

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2. a) D. H. Ohlendorf, J. D. Lipscomb, P. C. Weber, Nature 1988, 336, 403;
3. b) D. H. Ohlendorf, A. M. Orville, J. D. Lipscomb, J. Mol. Biol. 1994, 244, 586.
4. a) H. G. Jang, D. D. Cox, L. Que, Jr., J. Am. Chem. Soc. 1991, 113, 9200;
5. b) D. D. Cox, L. Que, Jr., ibid. 1988, 110, 8085;
6. c) M. G. Weller, U. Weser, ibid. 1982, 104, 3752.
7. 2 = catechol; cyclam = 1,4,8,11-tetraazacyclotetradecane.
8. The γ-lactone of the 3,5-di-tert-butylmuconic acid, 3,5-di-tert-butyl-5-carboxymethyl-2-furanone (1), is also an intradiol cleavage product.
9. a) T. Funabiki, T. Konishi, S. Kobayashi, A. Mizoguchi, M. Takano, S. Yoshida, Chem. Lett. 1987, 719.
10. b) Similar results with 2 as the main product were also obtained in our laboratory.
11. -3. Further details of the crystal structure investigation are available on request from the Fachinformationszentrum Karlsruhe, D-76344 Eggenstein-Leopoldshafen (Germany), on quoting the depository number CSD-401747.
12. a) H.-J. Krüger, Chem. Ber. 1995, 128, 531;
13. b) H.-J. Krüger, unpublished results.
14. 3,5-Di-tert-butyl-1,2-benzoquinone 2 was only produced in minor amounts (<1%).
15. III. In the oxidation of 3 in MeOH in the presence of thiocyanate, in addition to a few not yet identified products, the methyl ester of the γ-lactone could be identified as one of the products, indicating that at least to some extent intradiol cleavage did occur.
16. D. T. Sawyer, Oxygen Chemistry, Oxford University Press, New York, 1991, p. 21.
17. T. A. Walsh, D. P. Ballou, R. Mayer, L. Que, Jr., J. Biol. Chem. 1983, 258, 14422.
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