L-Tryptophan (ECMDB00929) (M2MDB000203)
| Record Information | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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| Version | 2.0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Creation Date | 2012-05-31 13:02:13 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Update Date | 2015-09-13 12:56:09 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Secondary Accession Numbers |
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| 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 |  | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Synonyms: |
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| 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. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| 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 |
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| Molecular Framework | Aromatic heteropolycyclic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| External Descriptors |
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| Physical Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| State: | Solid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Charge: | 0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Melting point: | 230 °C | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Experimental Properties: |
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| Predicted Properties |
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| 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: |
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| KEGG Pathways: | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| EcoCyc Pathways: |
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| Concentrations | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Find out more about how we convert literature concentrations. | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Spectra | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Spectra: | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| References | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| References: |
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| 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: |
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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