P. aeruginosa Metabolome Database: L-Tryptophan (PAMDB000203)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes Transporters

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 11:54:54 AM

Metabolite ID

PAMDB000203

Identification

Name:

L-Tryptophan

Description:

Tryptophan 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

🔍MOL SDF PDB SMILES InChI View Structure

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

Average Molecular Weight:

204.2252

Monoisotopic Molecular Weight:

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

Taxonomy Description

This compound belongs to the class of organic compounds known as indolyl carboxylic acids and derivatives. These are compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an indole ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indolyl carboxylic acids and derivatives

Direct Parent

Indolyl carboxylic acids and derivatives

Alternative Parents

Substituents

Indolyl carboxylic acid derivative
L-alpha-amino acid
Alpha-amino acid or derivatives
Alpha-amino acid
Indole
Aralkylamine
Amino fatty acid
Fatty acyl
Benzenoid
Substituted pyrrole
Heteroaromatic compound
Pyrrole
Azacycle
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Carbonyl group
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

L-alpha-amino acid (CHEBI:16828 )
erythrose 4-phosphate/phosphoenolpyruvate family amino acid (CHEBI:16828 )
tryptophan (CHEBI:16828 )
Common amino acids (C00078 )

Physical Properties

State:

Solid

Charge:

Melting point:

230 °C

Experimental Properties:

Property	Value	Source
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

Property	Value	Source
Water Solubility	1.36 mg/mL	ALOGPS
logP	-1.1	ALOGPS
logP	-1.1	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	2.54	ChemAxon
pKa (Strongest Basic)	9.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	79.11 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	56.2 m³·mol^-1	ChemAxon
Polarizability	21.05 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

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
Adenosine triphosphate + L-Tryptophan + tRNA(Trp) <> Adenosine monophosphate + Pyrophosphate + L-Tryptophanyl-tRNA(Trp)
L-Tryptophan + Water <> Hydrogen ion + Indole + Pyruvic acid + Ammonia
Adenosine triphosphate + L-Tryptophan + tRNA(Trp) > Adenosine monophosphate + Pyrophosphate + L-tryptophyl-tRNA(Trp)
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

Pathways:

Aminoacyl-tRNA biosynthesis pae00970
Glycine, serine and threonine metabolism pae00260
Metabolic pathways pae01100
Nitrogen metabolism pae00910
Phenylalanine, tyrosine and tryptophan biosynthesis pae00400
Tryptophan metabolism pae00380

Spectra

Spectra:

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)	splash10-0udi-0190000000-feaec8547634dddcad8c	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)	splash10-0udi-0390000000-45a6c4fd79081597d44a	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)	splash10-0udi-0290000000-34f7274f31a4cb321a0b	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)	splash10-0fk9-9270000000-9761607cbe821f87f172	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (1 TMS)	splash10-001i-0900000000-3faeed7ad32e1755c03c	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-0udi-0290000000-9c57a732e337fade3cb6	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS	Not Available
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-000i-0910000000-db5439a5499b19881720	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-014m-0900000000-cc4a579a29d19a1c0d44	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-00kf-3900000000-a931a9df4c855603d06e	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0a4i-0290000000-5fa576241f151a3a01a2	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0002-0900000000-417ea0b6e4e18e5fbde1	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000i-0900000000-38f5ce97d594f3e3f12d	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000i-0900000000-783ffff22f31096f238f	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0a4i-0290000000-3ced9d310dda312f8582	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0002-0900000000-a050919a36b995d34553	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000i-0900000000-1ddec73daead0ffadce4	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000i-0900000000-a8c9c60f075a675f6629	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0udi-0290602010-c09c931538bff74ac400	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0a4i-0900000000-0fed327c2a56f556e04c	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0udi-0090000000-98ec1c2c012e58eab924	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-00di-0090000000-fc77784da5d9b288d751	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0udi-0290601010-d6f94902c0cf639cb7bc	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0a4i-0900000000-27633a4f7ecfac45c730	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0udi-0090000000-ee6cb8392b2e8d644bc1	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-004i-0090000000-d81c86eceee1c9824b02	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0udi-0190000000-0e8b883dc8ab06c89d77	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0uxu-2940000000-cb35b9680612e19d8b3a	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-014i-2900000000-7cc592351cc616b1d75f	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-014i-1900000000-987615a0add5eb2c3169	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-014i-1900000000-f150d9d1e19c72d337a8	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-0a4r-0690000000-ea2d79df0b56be85abdd	View in MoNA
1D NMR	13C NMR Spectrum	Not Available
1D NMR	1H NMR Spectrum	Not Available
2D NMR	[1H,1H] 2D NMR Spectrum	Not Available
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available

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)

Links

External Links:

Resource	Link
CHEBI ID	27897
HMDB ID	HMDB00929
Pubchem Compound ID	6305
Kegg ID	C00078
ChemSpider ID	6066
Wikipedia	L-Tryptophan
BioCyc ID	TRP
EcoCyc ID	TRP
Ligand Expo	TRP_LFZW_DHE1

Enzymes

Protein Details

• Tryptophanyl-tRNA synthetase

General function:: Involved in nucleotide binding
Specific function:: ATP + L-tryptophan + tRNA(Trp) = AMP + diphosphate + L-tryptophyl-tRNA(Trp)
Gene Name:: trpS
Locus Tag:: PA4439
Molecular weight:: 49 kDa

Reactions

ATP + L-tryptophan + tRNA(Trp) = AMP + diphosphate + L-tryptophyl-tRNA(Trp).

Protein Details

• Tryptophan synthase alpha chain

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
Locus Tag:: PA0035
Molecular weight:: 28.5 kDa

Reactions

L-serine + 1-C-(indol-3-yl)glycerol 3-phosphate = L-tryptophan + glyceraldehyde 3-phosphate + H(2)O.

Protein Details

• Tryptophan synthase beta chain

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
Locus Tag:: PA0036
Molecular weight:: 43.7 kDa

Reactions

L-serine + 1-C-(indol-3-yl)glycerol 3-phosphate = L-tryptophan + glyceraldehyde 3-phosphate + H(2)O.

Transporters

Protein Details

• Uncharacterized amino-acid ABC transporter ATP-binding protein yecC

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
Locus Tag:: PA5152
Molecular weight:: 28.4 kDa

Protein Details

• Tryptophan-specific transport protein

General function:: Involved in amino acid transmembrane transporter activity
Specific function:: Involved in transporting tryptophan across the cytoplasmic membrane
Gene Name:: mtr
Locus Tag:: PA5434
Molecular weight:: 44.7 kDa

Protein Details

• Aromatic amino acid transport protein AroP

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
Locus Tag:: PA3000
Molecular weight:: 51 kDa

L-Tryptophan (PAMDB000203)

Structure for L-Tryptophan (PAMDB000203)

Enzymes

Reactions

Reactions

Reactions

Transporters