L-Tryptophan (YMDB00126)

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Identification

YMDB ID

YMDB00126

Name

L-Tryptophan

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

Tryptophan (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.

Structure

MOL SDF PDB SMILES InChI

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)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 number

73-22-3

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

IUPAC Name

(2S)-2-amino-3-(1H-indol-3-yl)propanoic acid

Traditional IUPAC Name

L-tryptophan

Chemical Formula

C₁₁H₁₂N₂O₂

SMILES

[H]OC(=O)[C@@]([H])(N([H])[H])C([H])([H])C1=C([H])N([H])C2=C1C([H])=C([H])C([H])=C2[H]

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.

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
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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

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

Physical Properties

State

Solid

Charge

Melting point

230 °C

Experimental Properties

Property	Value	Reference
Water Solubility	13.4 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]	PhysProp
LogP	-1.06 [HANSCH,C ET AL. (1995)]	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	1.36 g/L	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

extracellular
mitochondrion
cytoplasm

Organoleptic Properties

Not Available

SMPDB Pathways

NAD metabolism	PW002421
Tryptophan metabolism	PW002442

KEGG Pathways

Glycine, serine and threonine metabolism	ec00260
Phenylalanine, tyrosine and tryptophan biosynthesis	ec00400
Tryptophan metabolism	ec00380

SMPDB Reactions

L-Tryptophan + keto-phenylpyruvic acid → 3-(indol-3-yl)pyruvate + L-Phenylalanine

L-Tryptophan + oxygen → N'-Formylkynurenine

L-Tryptophan → oxygen + N'-Formylkynurenine

L-Tryptophan + Oxoglutaric acid → L-Glutamic acid + 3-(indol-3-yl)pyruvate

L-Serine + Indole → water + L-Tryptophan

KEGG Reactions

oxygen + L-Tryptophan → N-Formyl-L-kynurenine

L-Serine + 1-C-(indol-3-yl)glycerol 3-phosphate → D-Glyceraldehyde 3-phosphate + water + L-Tryptophan

Oxoglutaric acid + L-Tryptophan ↔ L-Glutamic acid + 3-(indol-3-yl)pyruvic acid

Adenosine triphosphate + tRNA(Trp) + L-Tryptophan → Adenosine monophosphate + Pyrophosphate + Trp-tRNA(Trp)

Concentrations

Intracellular Concentrations

Intracellular Concentration	Substrate	Growth Conditions	Strain	Citation
451 ± 23 µM	YEB media with 0.5 mM glucose	aerobic	Baker's yeast	Experimentally Determined Not Available
240 ± 70 µM	Synthetic medium with 20 g/L glucose	aerobic	Baker's yeast	PMID: 12584756
Conversion Details Here

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)	splash10-0udi-0190000000-feaec8547634dddcad8c	JSpectraViewer \| 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	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0udi-0290000000-34f7274f31a4cb321a0b	JSpectraViewer \| 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	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (1 TMS)	splash10-001i-0900000000-3faeed7ad32e1755c03c	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-0udi-0290000000-9c57a732e337fade3cb6	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-001i-0900000000-d054a214c1717940989f	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0udi-0290000000-9860799c854e5c9ac1c7	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0udi-0190000000-feaec8547634dddcad8c	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0udi-0390000000-45a6c4fd79081597d44a	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0udi-0290000000-34f7274f31a4cb321a0b	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-QQ (Non-derivatized)	splash10-0udi-3729000000-86129db57aaf1a245f93	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0fk9-9270000000-9761607cbe821f87f172	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-001i-0900000000-3faeed7ad32e1755c03c	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0udi-0290000000-9c57a732e337fade3cb6	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0560-4900000000-fa932bc4cffed0ca66b7	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00e9-9560000000-6829a8b2a2096883999f	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0udi-0290602010-c09c931538bff74ac400	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0a4i-0900000000-0fed327c2a56f556e04c	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0udi-0090000000-98ec1c2c012e58eab924	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-00di-0090000000-fc77784da5d9b288d751	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0udi-0290601010-d6f94902c0cf639cb7bc	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0a4i-0900000000-27633a4f7ecfac45c730	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0udi-0090000000-ee6cb8392b2e8d644bc1	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-004i-0090000000-d81c86eceee1c9824b02	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0udi-0190000000-0e8b883dc8ab06c89d77	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0uxu-2940000000-cb35b9680612e19d8b3a	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-014i-2900000000-7cc592351cc616b1d75f	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-014i-1900000000-987615a0add5eb2c3169	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-014i-1900000000-f150d9d1e19c72d337a8	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-0uxr-2960000000-f4c878f3abb1609bb5c5	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0udi-0090000000-c73c9b49139319c80b18	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0gb9-0930000000-da94834297fcc5b3d3c5	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-014i-0900000000-94061fd1f6b08445cdf3	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-014i-0900000000-e78172f4f27df232466e	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-014i-0900000000-93406e2cdb79770abc7d	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0udi-0190000000-0e8b883dc8ab06c89d77	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0uxu-2940000000-cb35b9680612e19d8b3a	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-014i-2900000000-5187dac98dbd6834d6ba	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-014i-1900000000-987615a0add5eb2c3169	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-014i-1900000000-174bb4d4390c75ae9a09	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0a4i-0900000000-0fed327c2a56f556e04c	JSpectraViewer \| MoNA
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
2D NMR	[1H,1H] 2D NMR Spectrum	Not Available	JSpectraViewer
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	JSpectraViewer

References

References:

UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
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:

Resource	Link
CHEBI ID	16828
HMDB ID	HMDB00929
Pubchem Compound ID	6305
Kegg ID	C00078
ChemSpider ID	6066
FOODB ID	FDB002250
Wikipedia	Tryptophan
BioCyc ID	TRP

Enzymes

Protein Details

1. Tryptophanyl-tRNA synthetase, mitochondrial

General function:: Involved in nucleotide binding
Specific function:: ATP + L-tryptophan + tRNA(Trp) = AMP + diphosphate + L-tryptophyl-tRNA(Trp)
Gene Name:: MSW1
Uniprot ID:: P04803
Molecular weight:: 43015.10156

Reactions

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

Protein Details

2. Tryptophanyl-tRNA synthetase, cytoplasmic

General function:: Involved in nucleotide binding
Specific function:: ATP + L-tryptophan + tRNA(Trp) = AMP + diphosphate + L-tryptophyl-tRNA(Trp)
Gene Name:: WRS1
Uniprot ID:: Q12109
Molecular weight:: 49350.0

Reactions

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

Protein Details

3. Tryptophan synthase

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:: TRP5
Uniprot ID:: P00931
Molecular weight:: 76625.5

Reactions

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

Protein Details

4. Aromatic amino acid aminotransferase 2

General function:: Involved in transferase activity, transferring nitrogenous groups
Specific function:: Has aromatic amino acid transaminase activity and kynurenine aminotransferase activity
Gene Name:: ARO9
Uniprot ID:: P38840
Molecular weight:: 58527.0

Reactions

An aromatic amino acid + 2-oxoglutarate → an aromatic oxo acid + L-glutamate.

Protein Details

5. Aromatic amino acid aminotransferase 1

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:: ARO8
Uniprot ID:: P53090
Molecular weight:: 56177.30078

Reactions

An aromatic amino acid + 2-oxoglutarate → an aromatic oxo acid + L-glutamate.
L-2-aminoadipate + 2-oxoglutarate → 2-oxoadipate + L-glutamate

Protein Details

6. Indoleamine 2,3-dioxygenase family protein

General function:: Involved in heme binding
Specific function:: Required for biosynthesis of nicotinic acid
Gene Name:: BNA2
Uniprot ID:: P47125
Molecular weight:: 50774.80078

Reactions

Transporters

Protein Details

1. General amino-acid permease GAP1

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:: GAP1
Uniprot ID:: P19145
Molecular weight:: 65654.89844

Protein Details

2. Tryptophan permease

General function:: Involved in transport
Specific function:: Required for high-affinity tryptophan transport. Also transports cysteine, phenyalanine and tyrosine
Gene Name:: TAT2
Uniprot ID:: P38967
Molecular weight:: 65403.80078

Protein Details

3. Leu/Val/Ile amino-acid permease

General function:: Involved in transport
Specific function:: Permease for leucine, valine and isoleucine. Also transports cysteine, methionine, phenyalanine, tyrosine and tryptophan
Gene Name:: BAP2
Uniprot ID:: P38084
Molecular weight:: 67669.60156

Protein Details

4. Valine/tyrosine/tryptophan amino-acid permease 1

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:: TAT1
Uniprot ID:: P38085
Molecular weight:: 68756.89844

Protein Details

5. Valine amino-acid permease

General function:: Involved in transport
Specific function:: Involved in transport of isoleucine, leucine, valine, cysteine, methionine, phenylalanine, tyrosine and tryptophan
Gene Name:: BAP3
Uniprot ID:: P41815
Molecular weight:: 67364.39844

Structure for #<Compound:0xa6a3b230>

Enzymes

Reactions

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Reactions

Transporters