Record Information
Version2.0
Creation Date2012-05-31 13:02:13 -0600
Update Date2015-09-13 12:56:09 -0600
Secondary Accession Numbers
  • ECMDB00929
Identification
Name:L-Tryptophan
DescriptionTryptophan is an amino acid which is the precursor of serotonin. Plants and microorganisms commonly synthesize tryptophan 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. Metabolism of tryptophan to serotonin requires nutrients such as vitamin B6, niacin and glutathione. Niacin is an important metabolite of tryptophan. (Wikipedia)
Structure
Thumb
Synonyms:
  • (-)-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)propionate
  • (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-(3-Indolyl)-propionate
  • (S)-a-amino-b-(3-Indolyl)-propionic 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)-propionate
  • (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
  • (S)-α-amino-1H-Indole-3-propanoate
  • (S)-α-amino-1H-Indole-3-propanoic acid
  • (S)-α-amino-β-(3-Indolyl)-propionate
  • (S)-α-amino-β-(3-Indolyl)-propionic acid
  • (S)-α-amino-β-Indolepropionate
  • (S)-α-amino-β-Indolepropionic acid
  • (S)-α-Aminoindole-3-propionate
  • (S)-α-Aminoindole-3-propionic acid
  • 1-b-3-Indolylalanine
  • 1-beta-3-Indolylalanine
  • 1-β-3-Indolylalanine
  • 1b-3-Indolylalanine
  • 1beta-3-Indolylalanine
  • 1H-Indole-3-Alanine
  • 1β-3-Indolylalanine
  • 2-Amino-3-indolylpropanate
  • 2-Amino-3-indolylpropanic acid
  • 2-Amino-3-indolylpropanoate
  • 2-Amino-3-indolylpropanoic acid
  • 3-(1H-Indol-3-yl)-L-Alanine
  • 3-Indol-3-ylalanine
  • a-Aminoindole-3-propionate
  • a-Aminoindole-3-propionic acid
  • Alpha'-Amino-3-indolepropionate
  • Alpha'-Amino-3-indolepropionic acid
  • Alpha-Aminoindole-3-propionate
  • Alpha-Aminoindole-3-propionic acid
  • Ardeytropin
  • H-TRP-oh
  • Indole-3-alanine
  • Kalma
  • L-(-)-Tryptophan
  • L-a-amino-3-Indolepropionate
  • L-a-amino-3-Indolepropionic acid
  • L-a-Aminoindole-3-propionate
  • L-a-Aminoindole-3-propionic acid
  • L-alpha-Amino-3-indolepropionate
  • L-alpha-Amino-3-indolepropionic acid
  • L-alpha-Aminoindole-3-propionate
  • L-alpha-Aminoindole-3-propionic acid
  • L-b-3-Indolylalanine
  • L-beta-3-Indolylalanine
  • L-Tryptofan
  • L-Tryptophan
  • L-Tryptophane
  • L-α-amino-3-Indolepropionate
  • L-α-amino-3-Indolepropionic acid
  • L-α-Aminoindole-3-propionate
  • L-α-Aminoindole-3-propionic acid
  • L-β-3-Indolylalanine
  • Lopac-T-0254
  • Lyphan
  • Optimax
  • Pacitron
  • Sedanoct
  • Triptofano
  • Trofan
  • Trp
  • Tryptacin
  • Tryptan
  • Tryptophan
  • Tryptophane
  • Tryptophanum
  • W
  • α-Aminoindole-3-propionate
  • α-Aminoindole-3-propionic acid
Chemical Formula:C11H12N2O2
Weight:Average: 204.2252
Monoisotopic: 204.089877638
InChI Key:QIVBCDIJIAJPQS-VIFPVBQESA-N
InChI:InChI=1S/C11H12N2O2/c12-9(11(14)15)5-7-6-13-10-4-2-1-3-8(7)10/h1-4,6,9,13H,5,12H2,(H,14,15)/t9-/m0/s1
CAS number:73-22-3
IUPAC Name:(2S)-2-amino-3-(1H-indol-3-yl)propanoic acid
Traditional IUPAC Name:L-tryptophan
SMILES:N[C@@H](CC1=CNC2=CC=CC=C12)C(O)=O
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
Substituents
  • 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
State:Solid
Charge:0
Melting point:230 °C
Experimental Properties:
PropertyValueSource
Water Solubility:13.4 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]; 23.5 mg/mL [HMP experimental]PhysProp
LogP:-1.06 [HANSCH,C ET AL. (1995)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility1.36 g/LALOGPS
logP-1.1ALOGPS
logP-1.1ChemAxon
logS-2.2ALOGPS
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Indole + L-Serine > Water + L-Tryptophan
Indoleglycerol phosphate + L-Serine > D-Glyceraldehyde 3-phosphate + Water + L-Tryptophan
N-Methyltryptophan + Water + Oxygen > Formaldehyde + Hydrogen peroxide + L-Tryptophan
Adenosine triphosphate + tRNA(Trp) + L-Tryptophan + tRNA(Trp) <> Adenosine monophosphate + Pyrophosphate + L-Tryptophanyl-tRNA(Trp)
Water + L-Tryptophan <> Indole + Ammonium + Pyruvic acid
L-Tryptophan + Water <> Indole + Pyruvic acid + Ammonia
L-Serine + Indole <> L-Tryptophan + Water
L-Serine + Indoleglycerol phosphate <> L-Tryptophan + D-Glyceraldehyde 3-phosphate + Water
Adenosine triphosphate + L-Tryptophan + tRNA(Trp) <> Adenosine monophosphate + Pyrophosphate + L-Tryptophanyl-tRNA(Trp)
L-Tryptophan + Water <> Hydrogen ion + Indole + Pyruvic acid + Ammonia
N-methyl-L-tryptophan + Water + Oxygen > L-Tryptophan + Formaldehyde + Hydrogen peroxide
Adenosine triphosphate + L-Tryptophan + tRNA(Trp) > Adenosine monophosphate + Pyrophosphate + L-tryptophyl-tRNA(Trp)
L-Tryptophan + Water > Indole + Pyruvic acid + Ammonia
L-Serine + Indoleglycerol phosphate > L-Tryptophan + glyceraldehyde 3-phosphate + Water
L-Tryptophan + Water + 2-Aminoacrylic acid + 2-Iminopropanoate <> Indole + Pyruvic acid + Ammonia
L-Serine + Indoleglycerol phosphate + Indole <> L-Tryptophan + D-Glyceraldehyde 3-phosphate + Water
L-Tryptophan + Adenosine triphosphate + Hydrogen ion + tRNA(Trp) > Adenosine monophosphate + Pyrophosphate + L-tryptophyl-tRNA(Trp)
Indole + L-Serine + L-Serine > Water + L-Tryptophan
L-Tryptophan > Hydrogen ion + Indole + 2-Aminoacrylic acid
Indole + L-Serine > Water + L-Tryptophan
Adenosine triphosphate + tRNA(Trp) + L-Tryptophan <> Adenosine monophosphate + Pyrophosphate + L-Tryptophanyl-tRNA(Trp)
Indole + L-Serine > Water + L-Tryptophan
L-Serine + Indole <> L-Tryptophan + Water
Adenosine triphosphate + tRNA(Trp) + L-Tryptophan <> Adenosine monophosphate + Pyrophosphate + L-Tryptophanyl-tRNA(Trp)
SMPDB Pathways:
Nitrogen metabolismPW000755 ThumbThumb?image type=greyscaleThumb?image type=simple
Trp OperonPW000965 ThumbThumb?image type=greyscaleThumb?image type=simple
Trp Operon InactivationPW000966 ThumbThumb?image type=greyscaleThumb?image type=simple
Tryptophan metabolismPW000815 ThumbThumb?image type=greyscaleThumb?image type=simple
inner membrane transportPW000786 ThumbThumb?image type=greyscaleThumb?image type=simple
tRNA Charging 2PW000803 ThumbThumb?image type=greyscaleThumb?image type=simple
tRNA chargingPW000799 ThumbThumb?image type=greyscaleThumb?image type=simple
tryptophan metabolism IIPW001916 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:
Concentrations
ConcentrationStrainMediaGrowth StatusGrowth SystemTemperatureDetails
12± 0 uMK12 NCM3722Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glucoseMid-Log PhaseShake flask and filter culture37 oCPMID: 19561621
24± 0 uMK12 NCM3722Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glycerolMid-Log PhaseShake flask and filter culture37 oCPMID: 19561621
21± 0 uMK12 NCM3722Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L acetateMid-Log PhaseShake flask and filter culture37 oCPMID: 19561621
9± 0 uMBW2511348 mM Na2HPO4, 22 mM KH2PO4, 10 mM NaCl, 45 mM (NH4)2SO4, supplemented with 1 mM MgSO4, 1 mg/l thiamine·HCl, 5.6 mg/l CaCl2, 8 mg/l FeCl3, 1 mg/l MnCl2·4H2O, 1.7 mg/l ZnCl2, 0.43 mg/l CuCl2·2H2O, 0.6 mg/l CoCl2·2H2O and 0.6 mg/l Na2MoO4·2H2O. 4 g/L GlucoStationary Phase, glucose limitedBioreactor, pH controlled, O2 and CO2 controlled, dilution rate: 0.2/h37 oCPMID: 17379776
14± 1 uMBL21 DE3Luria-Bertani (LB) mediaStationary phase cultures (overnight culture)Shake flask37 oCExperimentally Determined
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Find out more about how we convert literature concentrations.
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-0udi-0190000000-feaec8547634dddcad8cView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-0udi-0390000000-45a6c4fd79081597d44aView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0udi-0290000000-34f7274f31a4cb321a0bView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-0fk9-9270000000-9761607cbe821f87f172View in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-001i-0900000000-3faeed7ad32e1755c03cView in MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0udi-0290000000-9c57a732e337fade3cb6View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-001i-0900000000-d054a214c1717940989fView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0udi-0290000000-9860799c854e5c9ac1c7View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udi-0190000000-feaec8547634dddcad8cView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udi-0390000000-45a6c4fd79081597d44aView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udi-0290000000-34f7274f31a4cb321a0bView in MoNA
GC-MSGC-MS Spectrum - GC-EI-QQ (Non-derivatized)splash10-0udi-3729000000-86129db57aaf1a245f93View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0fk9-9270000000-9761607cbe821f87f172View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-001i-0900000000-3faeed7ad32e1755c03cView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0udi-0290000000-9c57a732e337fade3cb6View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0560-4900000000-fa932bc4cffed0ca66b7View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00e9-9560000000-6829a8b2a2096883999fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-0910000000-db5439a5499b19881720View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-014m-0900000000-cc4a579a29d19a1c0d44View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00kf-3900000000-a931a9df4c855603d06eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0a4i-0290000000-5fa576241f151a3a01a2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0002-0900000000-417ea0b6e4e18e5fbde1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-0900000000-38f5ce97d594f3e3f12dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-0900000000-783ffff22f31096f238fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0a4i-0290000000-3ced9d310dda312f8582View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0002-0900000000-a050919a36b995d34553View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-0900000000-1ddec73daead0ffadce4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-0900000000-a8c9c60f075a675f6629View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0udi-0290602010-c09c931538bff74ac400View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0a4i-0900000000-0fed327c2a56f556e04cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0udi-0090000000-98ec1c2c012e58eab924View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-00di-0090000000-fc77784da5d9b288d751View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0udi-0290601010-d6f94902c0cf639cb7bcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0a4i-0900000000-27633a4f7ecfac45c730View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0udi-0090000000-ee6cb8392b2e8d644bc1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-004i-0090000000-d81c86eceee1c9824b02View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0udi-0190000000-0e8b883dc8ab06c89d77View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0uxu-2940000000-cb35b9680612e19d8b3aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-014i-2900000000-7cc592351cc616b1d75fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-014i-1900000000-987615a0add5eb2c3169View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-014i-1900000000-f150d9d1e19c72d337a8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0a4r-0690000000-ea2d79df0b56be85abddView in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • Bender KI, Lutsevich NF, Lutsevich AN, Kupchikov VV: [Endogenous metabolites as modulators of the transport of drugs by serum albumin] Farmakol Toksikol. 1990 May-Jun;53(3):72-80. Pubmed: 2201566
  • Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. Pubmed: 19561621
  • Buczko W, Cylwik D, Stokowska W: [Metabolism of tryptophan via the kynurenine pathway in saliva] Postepy Hig Med Dosw (Online). 2005;59:283-9. Pubmed: 15995595
  • Cynober LA: Plasma amino acid levels with a note on membrane transport: characteristics, regulation, and metabolic significance. Nutrition. 2002 Sep;18(9):761-6. Pubmed: 12297216
  • Dunner DL, Heiber S, Perel JM: The effect of L-tryptophan administration on the concentration of probenecid in plasma and cerebrospinal fluid in patients. Psychopharmacology (Berl). 1977 Aug 16;53(3):305-8. Pubmed: 408860
  • Eklundh T, Eriksson M, Sjoberg S, Nordin C: Monoamine precursors, transmitters and metabolites in cerebrospinal fluid: a prospective study in healthy male subjects. J Psychiatr Res. 1996 May-Jun;30(3):201-8. Pubmed: 8884658
  • George CF, Millar TW, Hanly PJ, Kryger MH: The effect of L-tryptophan on daytime sleep latency in normals: correlation with blood levels. Sleep. 1989 Aug;12(4):345-53. Pubmed: 2669092
  • Guchhait RB, Janson C, Price WH: Validity of plasma factor in schizophrenia as measured by tryptophan uptake. Biol Psychiatry. 1975 Jun;10(3):303-14. Pubmed: 49200
  • Gutsche B, Grun C, Scheutzow D, Herderich M: Tryptophan glycoconjugates in food and human urine. Biochem J. 1999 Oct 1;343 Pt 1:11-9. Pubmed: 10493906
  • Heiman-Patterson TD, Bird SJ, Parry GJ, Varga J, Shy ME, Culligan NW, Edelsohn L, Tatarian GT, Heyes MP, Garcia CA, et al.: Peripheral neuropathy associated with eosinophilia-myalgia syndrome. Ann Neurol. 1990 Oct;28(4):522-8. Pubmed: 2174666
  • Heyes MP, Saito K, Crowley JS, Davis LE, Demitrack MA, Der M, Dilling LA, Elia J, Kruesi MJ, Lackner A, et al.: Quinolinic acid and kynurenine pathway metabolism in inflammatory and non-inflammatory neurological disease. Brain. 1992 Oct;115 ( Pt 5):1249-73. Pubmed: 1422788
  • Ishii, N., Nakahigashi, K., Baba, T., Robert, M., Soga, T., Kanai, A., Hirasawa, T., Naba, M., Hirai, K., Hoque, A., Ho, P. Y., Kakazu, Y., Sugawara, K., Igarashi, S., Harada, S., Masuda, T., Sugiyama, N., Togashi, T., Hasegawa, M., Takai, Y., Yugi, K., Arakawa, K., Iwata, N., Toya, Y., Nakayama, Y., Nishioka, T., Shimizu, K., Mori, H., Tomita, M. (2007). "Multiple high-throughput analyses monitor the response of E. coli to perturbations." Science 316:593-597. Pubmed: 17379776
  • Jonas AJ, Butler IJ: Circumvention of defective neutral amino acid transport in Hartnup disease using tryptophan ethyl ester. J Clin Invest. 1989 Jul;84(1):200-4. Pubmed: 2472426
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Kennedy JS, Gwirtsman HE, Schmidt DE, Johnson BW, Fielstein E, Salomon RM, Shiavi RG, Ebert MH, Parris WC, Loosen PT: Serial cerebrospinal fluid tryptophan and 5-hydroxy indoleacetic acid concentrations in healthy human subjects. Life Sci. 2002 Aug 23;71(14):1703-15. Pubmed: 12137916
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • Koskiniemi M, Laakso J, Kuurne T, Laipio M, Harkonen M: Indole levels in human lumbar and ventricular cerebrospinal fluid and the effect of L-tryptophan administration. Acta Neurol Scand. 1985 Feb;71(2):127-32. Pubmed: 2580417
  • Peng CT, Wu KH, Lan SJ, Tsai JJ, Tsai FJ, Tsai CH: Amino acid concentrations in cerebrospinal fluid in children with acute lymphoblastic leukemia undergoing chemotherapy. Eur J Cancer. 2005 May;41(8):1158-63. Epub 2005 Apr 14. Pubmed: 15911239
  • Rainesalo S, Keranen T, Palmio J, Peltola J, Oja SS, Saransaari P: Plasma and cerebrospinal fluid amino acids in epileptic patients. Neurochem Res. 2004 Jan;29(1):319-24. Pubmed: 14992292
  • Sjoberg S, Eriksson M, Nordin C: L-thyroxine treatment and neurotransmitter levels in the cerebrospinal fluid of hypothyroid patients: a pilot study. Eur J Endocrinol. 1998 Nov;139(5):493-7. Pubmed: 9849813
  • Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. Pubmed: 19212411
  • Talbert AM, Tranter GE, Holmes E, Francis PL: Determination of drug-plasma protein binding kinetics and equilibria by chromatographic profiling: exemplification of the method using L-tryptophan and albumin. Anal Chem. 2002 Jan 15;74(2):446-52. Pubmed: 11811421
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • Vijayendran, C., Barsch, A., Friehs, K., Niehaus, K., Becker, A., Flaschel, E. (2008). "Perceiving molecular evolution processes in Escherichia coli by comprehensive metabolite and gene expression profiling." Genome Biol 9:R72. Pubmed: 18402659
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
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.
Material Safety Data Sheet (MSDS)Download (PDF)
External Links:
ResourceLink
CHEBI ID27897
HMDB IDHMDB00929
Pubchem Compound ID6305
Kegg IDC00078
ChemSpider ID6066
WikipediaL-Tryptophan
BioCyc IDTRP
EcoCyc IDTRP
Ligand ExpoTRP_LFZW_DHE1

Enzymes

General function:
Involved in nucleotide binding
Specific function:
ATP + L-tryptophan + tRNA(Trp) = AMP + diphosphate + L-tryptophyl-tRNA(Trp)
Gene Name:
trpS
Uniprot ID:
P00954
Molecular weight:
37438
Reactions
ATP + L-tryptophan + tRNA(Trp) = AMP + diphosphate + L-tryptophyl-tRNA(Trp).
General function:
Involved in lyase activity
Specific function:
L-tryptophan + H(2)O = indole + pyruvate + NH(3)
Gene Name:
tnaA
Uniprot ID:
P0A853
Molecular weight:
52773
Reactions
L-tryptophan + H(2)O = indole + pyruvate + NH(3).
General function:
Involved in catalytic activity
Specific function:
The alpha subunit is responsible for the aldol cleavage of indoleglycerol phosphate to indole and glyceraldehyde 3- phosphate
Gene Name:
trpA
Uniprot ID:
P0A877
Molecular weight:
28724
Reactions
L-serine + 1-C-(indol-3-yl)glycerol 3-phosphate = L-tryptophan + glyceraldehyde 3-phosphate + H(2)O.
General function:
Involved in catalytic activity
Specific function:
The beta subunit is responsible for the synthesis of L- tryptophan from indole and L-serine
Gene Name:
trpB
Uniprot ID:
P0A879
Molecular weight:
42983
Reactions
L-serine + 1-C-(indol-3-yl)glycerol 3-phosphate = L-tryptophan + glyceraldehyde 3-phosphate + H(2)O.
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidative demethylation of N-methyl-L- tryptophan. Can also use other N-methyl amino acids, including sarcosine, which, however, is a poor substrate
Gene Name:
solA
Uniprot ID:
P40874
Molecular weight:
40902
Reactions
N-methyl-L-tryptophan + H(2)O + O(2) = L-tryptophan + formaldehyde + H(2)O(2).

Transporters

General function:
Involved in nucleotide binding
Specific function:
Probably part of a binding-protein-dependent transport system yecCS for an amino acid. Probably responsible for energy coupling to the transport system
Gene Name:
yecC
Uniprot ID:
P37774
Molecular weight:
27677
General function:
Involved in transporter activity
Specific function:
Probably part of the binding-protein-dependent transport system yecCS for an amino acid; probably responsible for the translocation of the substrate across the membrane
Gene Name:
yecS
Uniprot ID:
P0AFT2
Molecular weight:
24801
General function:
Involved in amino acid transmembrane transporter activity
Specific function:
Involved in transporting tryptophan across the cytoplasmic membrane
Gene Name:
mtr
Uniprot ID:
P0AAD2
Molecular weight:
44332
General function:
Involved in transport
Specific function:
Permease that is involved in the transport across the cytoplasmic membrane of the aromatic amino acids (phenylalanine, tyrosine, and tryptophan)
Gene Name:
aroP
Uniprot ID:
P15993
Molecular weight:
49690
General function:
Involved in amino acid transmembrane transporter activity
Specific function:
Involved in tryptophan transport across the cytoplasmic membrane. Plays a role in transporting tryptophan which is to be used catabolically
Gene Name:
tnaB
Uniprot ID:
P23173
Molecular weight:
45210
General function:
Involved in transporter activity
Specific function:
Non-specific porin
Gene Name:
ompN
Uniprot ID:
P77747
Molecular weight:
41220
General function:
Carbohydrate transport and metabolism
Specific function:
Specific function unknown
Gene Name:
yddG
Uniprot ID:
P46136
Molecular weight:
31539
General function:
Involved in transporter activity
Specific function:
Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
Gene Name:
phoE
Uniprot ID:
P02932
Molecular weight:
38922
General function:
Involved in transporter activity
Specific function:
OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
Gene Name:
ompF
Uniprot ID:
P02931
Molecular weight:
39333
General function:
Involved in transporter activity
Specific function:
Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
Gene Name:
ompC
Uniprot ID:
P06996
Molecular weight:
40368