Characterization of a new enzyme system that desaturates the side chain of N-acetyldopamine

A novel enzyme system that desaturates the side chain of the catecholamine derivative, N-acetyldopamine (NADA), was isolated and characterized from the larval cuticle of Sarcophaga bullata. The NADA desaturase system which converts NADA to 1,2-dehydro-NADA, surprisingly, does not resemble dehydrogen...

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Bibliographic Details
Published in:FEBS letters 1989-07, Vol.251 (1), p.69-73
Main Authors: Saul, Steven J., Sugumaran, Manickam
Format: Article
Language:English
Subjects:
Analytical, structural and metabolic biochemistry
Animals
Aromatic and heterocyclic compounds
Biological and medical sciences
Catecholamine metabolism
Chromatography, High Pressure Liquid
Cuticular tanning
Dehydro- N-acetyldopamine
dehydro-NADA, 1,2-dehydro-N-acetyldopamine
Diptera
Dopamine - analogs & derivatives
Dopamine - metabolism
Fundamental and applied biological sciences. Psychology
Heterocyclic compounds, pigments
Insecta - enzymology
Larva - enzymology
NADA, N-acetyldopamine
NANE, N-acetylnorepinephrine
Other biological molecules
Oxidation-Reduction
Oxidoreductases - isolation & purification
Oxidoreductases - metabolism
Phenoloxidase
Quinone isomerase
Quinone methide
Quinones - metabolism
Sarcophaga bullata
Sarcophagidae
Spectrophotometry, Ultraviolet
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Summary:A novel enzyme system that desaturates the side chain of the catecholamine derivative, N-acetyldopamine (NADA), was isolated and characterized from the larval cuticle of Sarcophaga bullata. The NADA desaturase system which converts NADA to 1,2-dehydro-NADA, surprisingly, does not resemble dehydrogenases such as succinate dehydrogenase. It uniquely performs the desaturation reaction by oxidizing NADA to its corresponding quinone and subsequently converting the resultant quinone to 1,2-dehydro-NADA via NADA quinone methide. Accordingly, desaturase enzyme preparation contained both o-diphenoloxidase activity and NADA quinone:NADA quinone methide isomerase activity. In addition, inhibition studies as well as trapping experiments also confirmed the obligatory formation of NADA quinone as the transient intermediate of the NADA desaturation. It is the first report of a cell-free system causing the side chain desaturation of any catecholamine derivative.
ISSN:0014-5793
1873-3468
DOI:10.1016/0014-5793(89)81430-9