Melatonin is a hormone derived from serotonin. It is produced in the brain’s light-sensitive pineal gland. The pineal’s secretion of melatonin is depressed by nerve impulses that originate in the retina of the eye and other light-sensitive tissue in the body in response to light. Pineal function is involved in circadian rhythms, patterns of biochemical activity associated with light and dark, such as sleep/wake cycles. Melatonin is also a powerful antioxidant, especially in the central nervous system. After serotonin (5-hydroxytryptamine) is produced in the pineal gland, it is converted to 5-hydroxy-N-acetyltryptamine by N-acetyltransferase. 5-Hydroxy-Nacetyltryptamine is then methylated by O-methyltransferase. SAM is the methylating agent. With this information, draw the synthetic pathway of melatonin.

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Melatonin is a hormone derived from serotonin. It is produced in the brain’s light-sensitive pineal
gland. The pineal’s secretion of melatonin is depressed by nerve impulses that originate in the
retina of the eye and other light-sensitive tissue in the body in response to light. Pineal function is
involved in circadian rhythms, patterns of biochemical activity associated with light and dark,
such as sleep/wake cycles. Melatonin is also a powerful antioxidant, especially in the central
nervous system. After serotonin (5-hydroxytryptamine) is produced in the pineal gland, it is
converted to 5-hydroxy-N-acetyltryptamine by N-acetyltransferase. 5-Hydroxy-Nacetyltryptamine
is then methylated by O-methyltransferase. SAM is the methylating agent. With
this information, draw the synthetic pathway of melatonin.

Expert Solution
Step 1

Melatonin is a hormone that is produced by the pineal gland in the human body. It is said to be associated with the human sleep-wake cycle. Melatonin is a treatment for insomnia, jet lag, etc.

Step 2

Melatonin is synthesized in the body from tryptophan. Tryptophan is converted to 5-hydroxytryptophan by tryptophan hydroxylase. The synthesis is as follows:

Biochemistry homework question answer, step 2, image 1

5-Hydroxy-Nacetyltryptamine or N-acetylserotonin is acted upon by acetylserotonin O-methyl transferase with SAM as a methyl donor to form melatonin.

 

 

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