On the Structure of Flavin-Oxygen Intermediates Involved in Enzymatic Reactions

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1977
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Entsch, Barrie
Massey, Vincent
Husein, Mazhar
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European Journal of Biochemistry. 1977, 76(1), pp. 139-148. ISSN 0014-2956. eISSN 1432-1033. Available under: doi: 10.1111/j.1432-1033.1977.tb11579.x
Zusammenfassung

During the catalytic reactions of flavoprotein hydroxylases and bacterial luciferase, flavin peroxides are formed as intermediates [see Massey, V. and Hemmerich, P. (1976) in The Enzymes, 3rd edn (P. Boyer, ed.) pp. 421 - 505, Academic Press, New York]. These intermediates have been postulated to be C(4a) derivatives of the flavin coenzyme. To test this hypothesis, modified flavin coenzymes carrying an oxygen substituent at position C(4a) of the isoalloxazine ring were synthesized. They are tightly bound by the apoenzymes of D-amino acid oxidase, p-hydroxybenzoate hydroxylase and lactate oxidase ; the resulting complexes show spectral properties closely similar to those of the transient oxygen adducts of the hydroxylases. The optical spectra of the lumiflavin model compounds were found to be highly dependent on the solvent environment and nature of the substituents. Under appropriate conditions they simulate satisfactorily the spectra of the transient enzymatic oxygen adducts. The results support the proposal that the primary oxygen adducts formed with these flavoproteins on reaction of the reduced enzymes with oxygen are flavin C(4a) peroxides.

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570 Biowissenschaften, Biologie
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ISO 690GHISLA, Sandro, Barrie ENTSCH, Vincent MASSEY, Mazhar HUSEIN, 1977. On the Structure of Flavin-Oxygen Intermediates Involved in Enzymatic Reactions. In: European Journal of Biochemistry. 1977, 76(1), pp. 139-148. ISSN 0014-2956. eISSN 1432-1033. Available under: doi: 10.1111/j.1432-1033.1977.tb11579.x
BibTex
@article{Ghisla1977Struc-8806,
  year={1977},
  doi={10.1111/j.1432-1033.1977.tb11579.x},
  title={On the Structure of Flavin-Oxygen Intermediates Involved in Enzymatic Reactions},
  number={1},
  volume={76},
  issn={0014-2956},
  journal={European Journal of Biochemistry},
  pages={139--148},
  author={Ghisla, Sandro and Entsch, Barrie and Massey, Vincent and Husein, Mazhar}
}
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