Enzymatic O-Methylation of N-Acetylserotonin to Melatonin

@article{Axelrod1960EnzymaticOO,
  title={Enzymatic O-Methylation of N-Acetylserotonin to Melatonin},
  author={Julius Axelrod and Herbert Weissbach},
  journal={Science},
  year={1960},
  volume={131},
  pages={1312 - 1312}
}
An enzyme, hydroxyindole-O-methyl transferase, that can transfer the methyl group of S-adenosylmethionine to the hydroxy group of N-acetylserotonin to form the hormone melatonin is described. This enzyme, which is highly localized in the pineal gland, also O-methylates serotonin. 

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Estimation of the methylating capacity of the pineal gland. With special reference to indole metabolism

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One of the products of the reaction, S-adenosylhomocysteine was found to be a potent inhibitor, whereas the other product, melatonin, did not inhibit the bovine pineal gland enzyme, even at much higher concentrations.
...

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We are greatly indebted to Dr. A. B. Lerner for supplying us with beef pineal glands and melatonin