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Trends in Comparative Biochemistry & Physiology   Volumes    Volume 1  Issue 2
The third way of dopamine
Yoshishige Umebachi
Pages: 709 - 720
Number of pages: 12
Trends in Comparative Biochemistry & Physiology
Volume 1  Issue 2

Copyright © 1993 Research Trends. All rights reserved

Dopamine, norepinephrine and epinephrine are well known as physiologically active compounds. Melanin formation from dopamine is also known. In the present review, these two path-ways are referred to as the first and second ways of dopamine, respectively. If the side-chain of dopamine is N-acylated, however, such N-acyldopamines are neither physiologically active nor melanogenic. Instead, N-acyldopamines work as cross-linking agents of insect cuticular proteins and also constitute some insect pigments such as Papiliochromes. This is the third way of dopamine in the present review. When N-acyldopamines are oxidized to their o-quinones by phenoloxidase, amino or imino groups of some amino acids are bonded to either the benzene ring or the side-chain of the o-quinones. The former is the case for the quinone-tanning in insect sclerotization and the latter is the case for β-sclerotization mechanism. In the β-sclerotization, o-quinones of N-acyl-dopamines are known to take p-quinone methide structure, to the β-carbon or α,β-carbons of which amino or imino groups are bonded. This mechanism is also applicable to Papiliochrome II synthesis. The stereochemistry of β-substituted dopamine derivatives is also discussed. The third way of dopamine is important from a comparative biochemical point of view.
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