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SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionTryptophan (abbreviated as Trp or W) is an alpha-amino acid. The L-isomer is one of the 22 proteinogenic amino acids, i.e., the building blocks of proteins. It is classified as a nonpolar, aromatic amino acid, because of the hydrophobic nature of the indole side chain. L-Tryptophan is an electrically neutral amino acid. Tryptophan is synthesized from shikimic acid or anthranilate. The latter condenses with phosphoribosylpyrophosphate (PRPP), generating pyrophosphate as a by-product. After ring opening of the ribose moiety and following reductive decarboxylation, indole-3-glycerinephosphate is produced, which in turn is transformed into indole. In the last step, tryptophan synthase catalyzes the formation of tryptophan from indole and the amino acid serine. S. cerevisiae degrade the aromatic amino acids (tryptophan, phenylalanine, and tyrosine) via the Ehrlich pathway. This pathway consists of 3 steps: 1) deamination of the amino acid to the corresponding alpha-keto acid; 2) decarboxylation of the resulting alpha-keto acid to the respective aldehyde; and, 3) reduction of the aldehyde to form the corresponding long chain or complex alcohol, known as a fusel alcohol or fusel oil. Fusel alcohols are important flavor and aroma compounds in yeast-fermented food products and beverages. The primary aminotransferase in tryptophan degradation is postulated to be Aro9p. In vitro studies demonstrated that Aro9p is active with phenylpyruvate, pyruvate, or p-hydroxyphenylpyruvate, but not 2-oxoglutarate as the amino acceptor. Aro9p is induced by aromatic amino acids and is subject to nitrogen regulation.
  • (-)-tryptophan
  • (2S)-2-amino-3-(1H-indol-3-yl)propanoate
  • (2S)-2-amino-3-(1H-indol-3-yl)propanoic acid
  • (l)-tryptophan
  • (S)-1H-Indole-3-alanine
  • (S)-2-Amino-3-(3-indolyl)propionic acid
  • (S)-a-Amino-1H-indole-3-propanoate
  • (S)-a-Amino-1H-indole-3-propanoic acid
  • (s)-a-amino-b-indolepropionate
  • (s)-a-amino-b-indolepropionic acid
  • (S)-a-Aminoindole-3-propionate
  • (S)-a-Aminoindole-3-propionic acid
  • (S)-alpha-Amino-1H-indole-3-propanoate
  • (S)-alpha-Amino-1H-indole-3-propanoic acid
  • (S)-alpha-Amino-beta-(3-indolyl)-propionic acid
  • (s)-alpha-amino-beta-indolepropionate
  • (s)-alpha-amino-beta-indolepropionic acid
  • (S)-alpha-Aminoindole-3-propionate
  • (S)-alpha-Aminoindole-3-propionic acid
  • (s)-tryptophan
  • 1-beta-3-Indolylalanine
  • 1beta-3-Indolylalanine
  • 1H-Indole-3-Alanine
  • 2-Amino-3-indolylpropanoate
  • 2-Amino-3-indolylpropanoic acid
  • 3-(1H-indol-3-yl)-L-Alanine
  • 3-Indol-3-ylalanine
  • alpha-Aminoindole-3-propionic acid
  • alpha'-Amino-3-indolepropionic acid
  • Ardeytropin
  • H-TRP-oh
  • Indole-3-alanine
  • Kalma
  • L-(-)-tryptophan
  • L-alpha-amino-3-indolepropionic acid
  • L-alpha-aminoindole-3-propionic acid
  • l-b-3-Indolylalanine
  • L-beta-3-indolylalanine
  • L-tryptofan
  • L-Tryptophan
  • L-tryptophane
  • Lyphan
  • Optimax
  • Pacitron
  • Sedanoct
  • Triptofano
  • Trofan
  • Tryptacin
  • Tryptan
  • Tryptophan
  • Tryptophane
  • Tryptophanum
  • Trp
  • W
  • (S)-Α-amino-1H-indole-3-propanoate
  • (S)-Α-amino-1H-indole-3-propanoic acid
  • (S)-a-Amino-b-(3-indolyl)-propionate
  • (S)-a-Amino-b-(3-indolyl)-propionic acid
  • (S)-alpha-Amino-beta-(3-indolyl)-propionate
  • (S)-Α-amino-β-(3-indolyl)-propionate
  • (S)-Α-amino-β-(3-indolyl)-propionic acid
  • L-Β-3-indolylalanine
  • Lopac-T-0254
  • Ardeydorm
  • L Tryptophan
  • L-Tryptophan-ratiopharm
  • Merck brand OF tryptophan
  • Niddapharm brand OF tryptophan
  • ICN brand OF tryptophan
  • Levotryptophan
  • PMS Tryptophan
  • PMS-Tryptophan
  • Ratiopharm brand OF tryptophan
  • Esparma brand OF tryptophan
  • Ratio-tryptophan
  • L Tryptophan ratiopharm
  • Naturruhe
  • Tryptophan metabolism alterations
  • Ardeypharm brand OF tryptophan
  • Kalma brand OF tryptophan
  • Pharmascience brand OF tryptophan
  • Upsher-smith brand OF tryptophan
  • Ratio tryptophan
CAS number73-22-3
WeightAverage: 204.2252
Monoisotopic: 204.089877638
IUPAC Name(2S)-2-amino-3-(1H-indol-3-yl)propanoic acid
Traditional IUPAC NameL-tryptophan
Chemical FormulaC11H12N2O2
Chemical Taxonomy
Description belongs to the class of organic compounds known as indolyl carboxylic acids and derivatives. Indolyl carboxylic acids and derivatives are compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an indole ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassIndolyl carboxylic acids and derivatives
Direct ParentIndolyl carboxylic acids and derivatives
Alternative Parents
  • Indolyl carboxylic acid derivative
  • Alpha-amino acid
  • Alpha-amino acid or derivatives
  • L-alpha-amino acid
  • 3-alkylindole
  • Indole
  • Aralkylamine
  • Benzenoid
  • Substituted pyrrole
  • Heteroaromatic compound
  • Pyrrole
  • Amino acid or derivatives
  • Amino acid
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Amine
  • Primary aliphatic amine
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Organonitrogen compound
  • Organooxygen compound
  • Primary amine
  • Organopnictogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
Melting point230 °C
Experimental Properties
Water Solubility13.4 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]PhysProp
LogP-1.06 [HANSCH,C ET AL. (1995)]PhysProp
Predicted Properties
Water Solubility1.36 g/LALOGPS
pKa (Strongest Acidic)2.54ChemAxon
pKa (Strongest Basic)9.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area79.11 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity56.2 m³·mol⁻¹ChemAxon
Polarizability21.05 ųChemAxon
Number of Rings2ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • extracellular
  • mitochondrion
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
NAD metabolismPW002421 ThumbThumb?image type=greyscaleThumb?image type=simple
Tryptophan metabolismPW002442 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Glycine, serine and threonine metabolismec00260 Map00260
Phenylalanine, tyrosine and tryptophan biosynthesisec00400 Map00400
Tryptophan metabolismec00380 Map00380
SMPDB Reactions
L-Tryptophan + keto-phenylpyruvic acid3-(indol-3-yl)pyruvate + L-Phenylalanine
L-Tryptophan + oxygenN'-Formylkynurenine
L-Tryptophanoxygen + N'-Formylkynurenine
L-Tryptophan + Oxoglutaric acidL-Glutamic acid + 3-(indol-3-yl)pyruvate
L-Serine + Indolewater + L-Tryptophan
KEGG Reactions
oxygen + L-TryptophanN-Formyl-L-kynurenine
L-Serine + 1-C-(indol-3-yl)glycerol 3-phosphateD-Glyceraldehyde 3-phosphate + water + L-Tryptophan
Oxoglutaric acid + L-TryptophanL-Glutamic acid + 3-(indol-3-yl)pyruvic acid
Adenosine triphosphate + tRNA(Trp) + L-TryptophanAdenosine monophosphate + Pyrophosphate + Trp-tRNA(Trp)
Intracellular Concentrations
Intracellular ConcentrationSubstrateGrowth ConditionsStrainCitation
451 ± 23 µM YEB media with 0.5 mM glucoseaerobicBaker's yeastExperimentally Determined
Not Available
240 ± 70 µM Synthetic medium with 20 g/L glucoseaerobicBaker's yeastPMID: 12584756
Conversion Details Here
Extracellular ConcentrationsNot Available
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  • Belenky, P., Christensen, K. C., Gazzaniga, F., Pletnev, A. A., Brenner, C. (2009). "Nicotinamide riboside and nicotinic acid riboside salvage in fungi and mammals. Quantitative basis for Urh1 and purine nucleoside phosphorylase function in NAD+ metabolism." J Biol Chem 284:158-164.19001417
  • Vuralhan, Z., Morais, M. A., Tai, S. L., Piper, M. D., Pronk, J. T. (2003). "Identification and characterization of phenylpyruvate decarboxylase genes in Saccharomyces cerevisiae." Appl Environ Microbiol 69:4534-4541.12902239
  • Vaseghi, S., Baumeister, A., Rizzi, M., Reuss, M. (1999). "In vivo dynamics of the pentose phosphate pathway in Saccharomyces cerevisiae." Metab Eng 1:128-140.10935926
  • Hans, M. A., Heinzle, E., Wittmann, C. (2003). "Free intracellular amino acid pools during autonomous oscillations in Saccharomyces cerevisiae." Biotechnol Bioeng 82:143-151.12584756
  • Schreve, J. L., Sin, J. K., Garrett, J. M. (1998). "The Saccharomyces cerevisiae YCC5 (YCL025c) gene encodes an amino acid permease, Agp1, which transports asparagine and glutamine." J Bacteriol 180:2556-2559.9573211
  • Nookaew, I., Jewett, M. C., Meechai, A., Thammarongtham, C., Laoteng, K., Cheevadhanarak, S., Nielsen, J., Bhumiratana, S. (2008). "The genome-scale metabolic model iIN800 of Saccharomyces cerevisiae and its validation: a scaffold to query lipid metabolism." BMC Syst Biol 2:71.18687109
  • Panozzo, C., Nawara, M., Suski, C., Kucharczyka, R., Skoneczny, M., Becam, A. M., Rytka, J., Herbert, C. J. (2002). "Aerobic and anaerobic NAD+ metabolism in Saccharomyces cerevisiae." FEBS Lett 517:97-102.12062417
  • Iraqui, I., Vissers, S., Cartiaux, M., Urrestarazu, A. (1998). "Characterisation of Saccharomyces cerevisiae ARO8 and ARO9 genes encoding aromatic aminotransferases I and II reveals a new aminotransferase subfamily." Mol Gen Genet 257:238-248.9491083
  • Castrillo, J. I., Zeef, L. A., Hoyle, D. C., Zhang, N., Hayes, A., Gardner, D. C., Cornell, M. J., Petty, J., Hakes, L., Wardleworth, L., Rash, B., Brown, M., Dunn, W. B., Broadhurst, D., O'Donoghue, K., Hester, S. S., Dunkley, T. P., Hart, S. R., Swainston, N., Li, P., Gaskell, S. J., Paton, N. W., Lilley, K. S., Kell, D. B., Oliver, S. G. (2007). "Growth control of the eukaryote cell: a systems biology study in yeast." J Biol 6:4.17439666
Synthesis Reference:Amir-Heidari, Bagher; Thirlway, Jenny; Micklefield, Jason. Stereochemical course of tryptophan dehydrogenation during biosynthesis of the calcium-dependent lipopeptide antibiotics. Organic Letters (2007), 9(8), 1513-1516.
External Links:
Pubchem Compound ID6305
Kegg IDC00078
ChemSpider ID6066


General function:
Involved in nucleotide binding
Specific function:
ATP + L-tryptophan + tRNA(Trp) = AMP + diphosphate + L-tryptophyl-tRNA(Trp)
Gene Name:
Uniprot ID:
Molecular weight:
ATP + L-tryptophan + tRNA(Trp) → AMP + diphosphate + L-tryptophyl-tRNA(Trp).
General function:
Involved in nucleotide binding
Specific function:
ATP + L-tryptophan + tRNA(Trp) = AMP + diphosphate + L-tryptophyl-tRNA(Trp)
Gene Name:
Uniprot ID:
Molecular weight:
ATP + L-tryptophan + tRNA(Trp) → AMP + diphosphate + L-tryptophyl-tRNA(Trp).
General function:
Involved in catalytic activity
Specific function:
L-serine + 1-C-(indol-3-yl)glycerol 3- phosphate = L-tryptophan + glyceraldehyde 3-phosphate + H(2)O
Gene Name:
Uniprot ID:
Molecular weight:
L-serine + 1-C-(indol-3-yl)glycerol 3-phosphate → L-tryptophan + glyceraldehyde 3-phosphate + H(2)O.
General function:
Involved in transferase activity, transferring nitrogenous groups
Specific function:
Has aromatic amino acid transaminase activity and kynurenine aminotransferase activity
Gene Name:
Uniprot ID:
Molecular weight:
An aromatic amino acid + 2-oxoglutarate → an aromatic oxo acid + L-glutamate.
General function:
Involved in transferase activity, transferring nitrogenous groups
Specific function:
Has aromatic amino acid transaminase activity. Also active with methionine, alpha-aminoadipate and leucine when phenylpyruvate is the amino acceptor
Gene Name:
Uniprot ID:
Molecular weight:
An aromatic amino acid + 2-oxoglutarate → an aromatic oxo acid + L-glutamate.
L-2-aminoadipate + 2-oxoglutarate → 2-oxoadipate + L-glutamate
General function:
Involved in heme binding
Specific function:
Required for biosynthesis of nicotinic acid
Gene Name:
Uniprot ID:
Molecular weight:


General function:
Involved in transport
Specific function:
Permease for various amino acids as well as for GABA. Can also transport L-cysteine and beta-alanine
Gene Name:
Uniprot ID:
Molecular weight:
General function:
Involved in transport
Specific function:
Required for high-affinity tryptophan transport. Also transports cysteine, phenyalanine and tyrosine
Gene Name:
Uniprot ID:
Molecular weight:
General function:
Involved in transport
Specific function:
Permease for leucine, valine and isoleucine. Also transports cysteine, methionine, phenyalanine, tyrosine and tryptophan
Gene Name:
Uniprot ID:
Molecular weight:
General function:
Involved in transport
Specific function:
High-affinity transport of valine and tyrosine. Low- affinity transport of tryptophan. Can also transport L-cysteine
Gene Name:
Uniprot ID:
Molecular weight:
General function:
Involved in transport
Specific function:
Involved in transport of isoleucine, leucine, valine, cysteine, methionine, phenylalanine, tyrosine and tryptophan
Gene Name:
Uniprot ID:
Molecular weight: