Syntheses of carbon-13 and deuterium labelled L-tryptophan, racemic 5-hydroxytryptophan and 5-hydroxytryptamine (serotonin)
✍ Scribed by Walfred S. Saari
- Publisher
- John Wiley and Sons
- Year
- 1982
- Tongue
- French
- Weight
- 414 KB
- Volume
- 19
- Category
- Article
- ISSN
- 0022-2135
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✦ Synopsis
Abstract
Convenient and efficient syntheses of ^13^C and ^2^H sidechain labelled L‐tryptophan, racemic 5‐hydroxytryptophan and 5‐hydroxytryptamine (serotonin) from indole and 5‐benzyloxyindole are described.
📜 SIMILAR VOLUMES
The aromatic amino acids tyrosine (TYR), 3,4-dihydroxyphenylalanine (DOPA) , tryptophan (TRP) and 5-hydroxytryptophan (5-HTP) are of especial interest because of their role as precursors for the neurotransmitters dopamine and serotonin, Scheme 1.
## Abstract The enzymatic synthesis of l‐tryptophan and its derivative 5′‐hydroxy‐l‐tryptophan labeled with deuterium and tritium at the α‐carbon position is reported. The mixture containing __S__‐methyl‐l‐cysteine, indole or 5‐hydroxyindole dissolved in deuteriated or tritiated water has been conv
For metabolic studies in this Laboratory, 5-hydroxytryptamine (serotonin) labelled with I4C in the pyrrole part of the indole ring was required. Previous attempts to reach this compound through Madelung cyclization of 3-benzyloxy--6-formylaminotoluene failed (I), although this way proved to be succe
## Abstract Robust and straightforward methods are described for the first syntheses of highly pure ^13^C‐ and ^14^C‐labelled __L__‐5‐benzylhydantoin (__L__‐BH) and __L__‐5‐indolylmethylhydantoin (__L__‐IMH) by cyclizing the amino acids __L__‐phenylalanine and __L__‐tryptophan, respectively, with p