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 Å²
H-bond donors: 3
H-bond acceptors: 3
Formal charge: 0

via PubChem

Research

80,629 papers

Kynurenines: Tryptophan's metabolites in exercise, inflammation, and mental health.ReviewScience (New York, N.Y.) · 2017Cervenka I, Agudelo LZ, Ruas JLDOI: 10.1126/science.aaf9794
The Role of Tryptophan Metabolites in Neuropsychiatric Disorders.ReviewInternational journal of molecular sciences · 2022Davidson M, Rashidi N, Nurgali K et al.DOI: 10.3390/ijms23179968
The Tryptophan Pathway Targeting Antioxidant Capacity in the Placenta.ReviewOxidative medicine and cellular longevity · 2018Xu K, Liu G, Fu CDOI: 10.1155/2018/1054797
Tryptophan in Multicomponent Petasis Reactions for Peptide Stapling and Late-Stage Functionalisation.Angewandte Chemie (International ed. in English) · 2023Krajcovicova S, Spring DRDOI: 10.1002/anie.202307782
Tryptophan phosphorescence at room temperature as a tool to study protein structure and dynamics.ReviewPhotochemistry and photobiology · 1989Papp S, Vanderkooi JMDOI: 10.1111/j.1751-1097.1989.tb05576.x
Longitudinal analysis of fecal tryptophan metabolites and microbiome composition in very preterm infants: impact of birth mode and feeding type.Gut microbes · 2025Wieser NV, van Schajik Y, Ghiboub M et al.DOI: 10.1080/19490976.2025.2541031
L-Tryptophan's effects on brain chemistry and sleep in cats and rats: a review.ReviewNeuroscience and biobehavioral reviews · 1982Radulovacki MDOI: 10.1016/0149-7634(82)90025-2
Directed Evolution of a Tryptophan 2,3-Dioxygenase for the Diastereoselective Monooxygenation of Tryptophans.Angewandte Chemie (International ed. in English) · 2020Wei Y, Lu C, Jiang S et al.DOI: 10.1002/anie.201911825

via PubMed

Wikidata facts

Mass: 204.09

Show 7 more facts

Commons category: Tryptophan
chemical formula: C₁₁H₁₂N₂O₂
canonical SMILES: C1=CC=C2C(=C1)C(=CN2)CC(C(=O)O)N
World Health Organisation international non-proprietary name: tryptophan
pKa: 9.39
isomeric SMILES: N[C@@H](CC1=CNC2=C1C=CC=C2)C(O)=O
NCI Thesaurus ID: C29603

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Article

22 sections

Contents

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).