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2-Aminobenzoyl-CoA monooxygenase/reductase, a novel type of flavoenzyme/reductase, a novel type of flavoenzyme : identification of the reaction products

2-Aminobenzoyl-CoA monooxygenase/reductase, a novel type of flavoenzyme/reductase, a novel type of flavoenzyme : identification of the reaction products

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LANGKAU, Bernd, Sandro GHISLA, Reiner BUDER, Klaus ZIEGLER, Georg FUCHS, 1990. 2-Aminobenzoyl-CoA monooxygenase/reductase, a novel type of flavoenzyme/reductase, a novel type of flavoenzyme : identification of the reaction products. In: European Journal of Biochemistry. 191(2), pp. 365-371. ISSN 0014-2956. eISSN 1432-1033. Available under: doi: 10.1111/j.1432-1033.1990.tb19131.x

@article{Langkau19902Amin-6775, title={2-Aminobenzoyl-CoA monooxygenase/reductase, a novel type of flavoenzyme/reductase, a novel type of flavoenzyme : identification of the reaction products}, year={1990}, doi={10.1111/j.1432-1033.1990.tb19131.x}, number={2}, volume={191}, issn={0014-2956}, journal={European Journal of Biochemistry}, pages={365--371}, author={Langkau, Bernd and Ghisla, Sandro and Buder, Reiner and Ziegler, Klaus and Fuchs, Georg} }

eng In a previous report we have described some properties of a novel flavoenzyme from a denitrifying Pseudomonas species which catalyzes the oxygen- and NAD(P)H-dependent conversion of 2-aminobenzoyl-CoA [Buder, R., Ziegler, K., Fuchs, G., Langkau, B. & Ghisla, S. (1989) Eur. J. Biochem. 185, 637 634]. In this paper, we report on the identification of the three products formed from 2-aminobenzoyl-CoA in this reaction. The spectroscopic data and the chemical properties of these compounds and those of their degradation products are compatible with the structures of 2-amino-5-hydroxybenzoyl-CoA, 2-amino-5-hydroxycyclohex-1-enecarboxyl-CoA and of 2-amino-5-oxocyclohex-1-enecarboxyl-CoA. The latter is the main product and was found to be rather unstable since it hydrolyzes and decarboxylates readily at pH < 5. Ammonia is released from the decarboxylation product in the neutral pH range to yield 1,4-cyclohexanedione. Conditions were optimized such that the CoA thioester of 2-amino-5-hydroxybenzoate is the product obtained at > 98% yield. 2-amino-5-hydroxycyclohex-1-enecarboxyl-CoA is the product which is formed when the mixture of the reaction products is treated with sodium borohydride before separation. Fuchs, Georg Langkau, Bernd Buder, Reiner Ghisla, Sandro Ziegler, Klaus First publ. in: European Journal of Biochemistry 191 (1990), 2, pp. 365-371 Ziegler, Klaus 2011-03-24T17:29:05Z Buder, Reiner 1990 Fuchs, Georg deposit-license application/pdf 2011-03-24T17:29:05Z Ghisla, Sandro Langkau, Bernd 2-Aminobenzoyl-CoA monooxygenase/reductase, a novel type of flavoenzyme/reductase, a novel type of flavoenzyme : identification of the reaction products

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