tryptophan
Also known as L-Trp, (-)-Tryptophan, (2S)-2-amino-3-(1H-indol-3-yl)Propanoic acid, (S)-alpha-amino-1H-indole-3-propanoic acid, (S)-alpha-Amino-beta-(3-indolyl)-propionic acid, (S)-Tryptophan, (S)-α-amino-1H-indole-3-propanoic acid, L-(-)-Tryptophan
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Chemical data
- Formula
- C11H12N2O2
- Molecular weight
- 204.22 g/mol
- IUPAC name
- (2S)-2-amino-3-(1H-indol-3-yl)propanoic acid
- SMILES
- C1=CC=C2C(=C1)C(=CN2)C[C@@H](C(=O)O)N
- InChIKey
- QIVBCDIJIAJPQS-VIFPVBQESA-N
- XLogP
- -1.1
- Polar surface area
- 79.1 Ų
- H-bond donors
- 3
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Research
80,629 papersArticle
22 sectionsContents
- Function
- Recommended dietary allowance
- Dietary sources
- Medical use
- Depression
- Insomnia
- Side effects
- Interactions
- Isolation
- Biosynthesis and industrial production
- Society and culture
- Showa Denko contamination scandal
- Turkey meat and drowsiness hypothesis
- Research
- Yeast amino acid metabolism
- Serotonin precursor
- Psychedelic effects
- Fluorescence
- See also
- References
- Further reading
- External links
thumb|Tryptophan ball and stick model spinning Tryptophan (symbol Trp or W) is an α-amino acid that is used in the biosynthesis of proteins. Tryptophan contains an α-amino group, an α-carboxylic acid group, and a side chain indole, making it a polar molecule with a non-polar aromatic beta carbon substituent. Tryptophan is also a precursor to the neurotransmitter serotonin, the hormone melatonin, and vitamin B3 (niacin). It is encoded by the codon UGG.
Like other amino acids, tryptophan is a zwitterion at physiological pH where the amino group is protonated (–; pKa = 9.39) and the carboxylic acid is deprotonated (–COO−; pKa = 2.38).