L-Tyrosine (ECMDB00158) (M2MDB000060)
| Record Information | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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| Version | 2.0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Creation Date | 2012-05-31 10:22:12 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Update Date | 2015-09-13 12:56:06 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Secondary Accession Numbers |
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| Identification | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Name: | L-Tyrosine | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Description | Tyrosine (Tyr, Y) or 4-hydroxyphenylalanine is a non-essential amino acid with a polar side group. Its codons are UAC and UAU. Aside from being a proteogenic amino acid, tyrosine has a special role by virtue of the phenol functionality. It occurs in proteins that are part of signal transduction processes. It functions as a receiver of phosphate groups that are transferred by way of protein kinases (so-called receptor tyrosine kinases). Phosphorylation of the hydroxyl group changes the activity of the target protein. (Wikipedia) L-Tyrosine is the enantiomer of tyrosine (the other being D-tyrosine) that is used in building proteins. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Structure |  | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Synonyms: |
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| Chemical Formula: | C9H11NO3 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Weight: | Average: 181.1885 Monoisotopic: 181.073893223 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| InChI Key: | OUYCCCASQSFEME-QMMMGPOBSA-N | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| InChI: | InChI=1S/C9H11NO3/c10-8(9(12)13)5-6-1-3-7(11)4-2-6/h1-4,8,11H,5,10H2,(H,12,13)/t8-/m0/s1 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| CAS number: | 60-18-4 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| IUPAC Name: | (2S)-2-amino-3-(4-hydroxyphenyl)propanoic acid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Traditional IUPAC Name: | L-tyrosine | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| SMILES: | N[C@@H](CC1=CC=C(O)C=C1)C(O)=O | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Chemical Taxonomy | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Description | belongs to the class of organic compounds known as tyrosine and derivatives. Tyrosine and derivatives are compounds containing tyrosine or a derivative thereof resulting from reaction of tyrosine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Kingdom | Organic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Super Class | Organic acids and derivatives | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Class | Carboxylic acids and derivatives | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Sub Class | Amino acids, peptides, and analogues | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Direct Parent | Tyrosine and derivatives | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Alternative Parents |
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| Substituents |
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| Molecular Framework | Aromatic homomonocyclic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| External Descriptors |
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| Physical Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| State: | Solid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Charge: | 0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Melting point: | 343 °C | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Experimental Properties: |
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| Predicted Properties |
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| Biological Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Cellular Locations: | Cytoplasm | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Reactions: | alpha-Ketoglutarate + L-Tyrosine <> 4-Hydroxyphenylpyruvic acid + L-Glutamate Adenosine triphosphate + tRNA(Tyr) + L-Tyrosine + tRNA(Tyr) <> Adenosine monophosphate + Pyrophosphate + L-Tyrosyl-tRNA(Tyr) + L-Tyrosyl-tRNA(Tyr) S-Adenosylmethionine + NADPH + L-Tyrosine > p-Cresol + 5'-Deoxyadenosine + Dehydroglycine + Hydrogen ion + L-Methionine + NADP Water + Phosphotyrosine > Phosphate + L-Tyrosine Adenosine triphosphate + L-Tyrosine + tRNA(Tyr) <> Adenosine monophosphate + Pyrophosphate + L-Tyrosyl-tRNA(Tyr) C15815 + L-Tyrosine + Iminoglycine <> 4-Methyl-5-(2-phosphoethyl)-thiazole L-Tyrosine + S-Adenosylmethionine + a reduced electron acceptor > Dehydroglycine + p-Cresol + 5'-Deoxyadenosine + L-Methionine + an oxidized electron acceptor + Hydrogen ion L-Tyrosine + Oxoglutaric acid <> 4-Hydroxyphenylpyruvic acid + L-Glutamate Adenosine triphosphate + L-Tyrosine + tRNA(Tyr) > Adenosine monophosphate + Pyrophosphate + L-tyrosyl-tRNA(Tyr) L-Tyrosine + S-adenosyl-L-methionine + reduced acceptor > 2-iminoacetate + p-Cresol + 5'-Deoxyadenosine + L-Methionine + acceptor +2 Hydrogen ion L-Tyrosine + S-Adenosylmethionine + NADPH <> 2-iminoacetate + p-Cresol + 5'-Deoxyadenosine + L-Methionine + NADP + Hydrogen ion L-Tyrosine + Adenosine triphosphate + Hydrogen ion + tRNA(Tyr) + L-Tyrosine > Adenosine monophosphate + Pyrophosphate + L-tyrosyl-tRNA(Tyr) 4-hydroxyphenylpyruvate + L-Glutamic acid + L-Glutamate > Oxoglutaric acid + L-Tyrosine + L-Tyrosine L-Tyrosine + NADPH + S-adenosyl-L-methionine + L-Tyrosine + NADPH > Hydrogen ion + NADP + L-Methionine + 5'-Deoxyadenosine + p-Cresol + 2-iminoacetate L-Tyrosine + S-adenosyl-L-methionine + NADPH > Dehydroglycine + 4-Methylcatechol + 5'-Deoxyadenosine + L-Methionine + NADP + Hydrogen ion C15815 + L-Tyrosine + 2-iminoacetate <>4 4-Methyl-5-(2-phosphoethyl)-thiazole Adenosine triphosphate + tRNA(Tyr) + L-Tyrosine <> Adenosine monophosphate + Pyrophosphate + L-Tyrosyl-tRNA(Tyr) C15815 + L-Tyrosine + 2-iminoacetate <>4 4-Methyl-5-(2-phosphoethyl)-thiazole Adenosine triphosphate + tRNA(Tyr) + L-Tyrosine <> Adenosine monophosphate + Pyrophosphate + L-Tyrosyl-tRNA(Tyr) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| SMPDB Pathways: |
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| KEGG Pathways: |
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| EcoCyc Pathways: |
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| Concentrations | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Find out more about how we convert literature concentrations. | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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| References | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| References: |
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| Synthesis Reference: | Enei, Hitoshi; Matsui, Hiroshi; Yamashita, Koichi; Okumura, Shinji; Yamada, Hideaki. Microbiological synthesis of L-tyrosine and 3,4-dihydroxyphenyl-L-alanine. I. Distribution of tyrosine phenol lyase in microorganisms. Agricultural and Biological Chemist | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Material Safety Data Sheet (MSDS) | Download (PDF) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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| External Links: |
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Enzymes
- General function:
- Involved in transferase activity
- Specific function:
- L-aspartate + 2-oxoglutarate = oxaloacetate + L-glutamate
- Gene Name:
- aspC
- Uniprot ID:
- P00509
- Molecular weight:
- 43573
Reactions
| L-aspartate + 2-oxoglutarate = oxaloacetate + L-glutamate. |
- General function:
- Involved in transferase activity
- Specific function:
- An aromatic amino acid + 2-oxoglutarate = an aromatic oxo acid + L-glutamate
- Gene Name:
- tyrB
- Uniprot ID:
- P04693
- Molecular weight:
- 43537
Reactions
| An aromatic amino acid + 2-oxoglutarate = an aromatic oxo acid + L-glutamate. |
- General function:
- Involved in transferase activity
- Specific function:
- L-histidinol phosphate + 2-oxoglutarate = 3- (imidazol-4-yl)-2-oxopropyl phosphate + L-glutamate
- Gene Name:
- hisC
- Uniprot ID:
- P06986
- Molecular weight:
- 39360
Reactions
| L-histidinol phosphate + 2-oxoglutarate = 3-(imidazol-4-yl)-2-oxopropyl phosphate + L-glutamate. |
- General function:
- Involved in acid phosphatase activity
- Specific function:
- A phosphate monoester + H(2)O = an alcohol + phosphate
- Gene Name:
- appA
- Uniprot ID:
- P07102
- Molecular weight:
- 47056
Reactions
| A phosphate monoester + H(2)O = an alcohol + phosphate. |
| Myo-inositol hexakisphosphate + H(2)O = 1D-myo-inositol 1,2,3,5,6-pentakisphosphate + phosphate. |
- General function:
- Involved in acid phosphatase activity
- Specific function:
- Dephosphorylates several organic phosphomonoesters and catalyzes the transfer of low-energy phosphate groups from phosphomonoesters to hydroxyl groups of various organic compounds. Preferentially acts on aryl phosphoesters. Might function as a broad-spectrum dephosphorylating enzyme able to scavenge both 3'- and 5'-nucleotides and also additional organic phosphomonoesters
- Gene Name:
- aphA
- Uniprot ID:
- P0AE22
- Molecular weight:
- 26103
Reactions
| A phosphate monoester + H(2)O = an alcohol + phosphate. |
- General function:
- Involved in nucleotide binding
- Specific function:
- Catalyzes the attachment of tyrosine to tRNA(Tyr) in a two-step reaction:tyrosine is first activated by ATP to form Tyr- AMP and then transferred to the acceptor end of tRNA(Tyr)
- Gene Name:
- tyrS
- Uniprot ID:
- P0AGJ9
- Molecular weight:
- 47527
Reactions
| ATP + L-tyrosine + tRNA(Tyr) = AMP + diphosphate + L-tyrosyl-tRNA(Tyr). |
- General function:
- Involved in catalytic activity
- Specific function:
- Catalyzes the rearrangement of 1-deoxy-D-xylulose 5- phosphate (DXP) to produce the thiazole phosphate moiety of thiamine. Sulfur is provided by the thiocarboxylate moiety of the carrier protein ThiS. In vitro, sulfur can be provided by H(2)S
- Gene Name:
- thiG
- Uniprot ID:
- P30139
- Molecular weight:
- 26896
Reactions
| 1-deoxy-D-xylulose 5-phosphate + 2-iminoacetate + thiocarboxy-adenylate-[sulfur-carrier protein ThiS] = 2-((2R,5Z)-2-carboxy-4-methylthiazol-5(2H)-ylidene)ethyl phosphate + [sulfur-carrier protein ThiS] + 2 H(2)O. |
- General function:
- Involved in catalytic activity
- Specific function:
- Catalyzes the radical-mediated cleavage of tyrosine to dehydroglycine and p-cresol
- Gene Name:
- thiH
- Uniprot ID:
- P30140
- Molecular weight:
- 43320
Reactions
| L-tyrosine + S-adenosyl-L-methionine + reduced acceptor = 2-iminoacetate + 4-methylphenol + 5'-deoxyadenosine + L-methionine + acceptor + 2 H(+). |
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 tyrosine across the cytoplasmic membrane
- Gene Name:
- tyrP
- Uniprot ID:
- P0AAD4
- Molecular weight:
- 42819
- 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 transport
- Specific function:
- Permease that is involved in the transport across the cytoplasmic membrane of phenylalanine
- Gene Name:
- pheP
- Uniprot ID:
- P24207
- Molecular weight:
- 50677
- 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