L-Isoleucine (ECMDB00172) (M2MDB000071)
| Record Information | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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| Version | 2.0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Creation Date | 2012-05-31 10:22:52 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Update Date | 2015-09-13 12:56:06 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Secondary Accession Numbers |
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| Identification | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Name: | L-Isoleucine | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Description | Isoleucine is an amino acid with the chemical formula HO2CCH(NH2)CH(CH3)CH2CH3. Its codons are AUU, AUC and AUA. With a hydrocarbon side chain, isoleucine is classified as a hydrophobic amino acid. Together with threonine, isoleucine is one of two common amino acids that have a chiral side chain. Four stereoisomers of isoleucine are possible, including two possible diastereomers of L-isoleucine. However, isoleucine present in nature exists in one enantiomeric form, (2S,3S)-2-amino-3-methylpentanoic acid. (Wikipedia) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Structure |  | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Synonyms: |
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| Chemical Formula: | C6H13NO2 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Weight: | Average: 131.1729 Monoisotopic: 131.094628665 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| InChI Key: | AGPKZVBTJJNPAG-WHFBIAKZSA-N | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| InChI: | InChI=1S/C6H13NO2/c1-3-4(2)5(7)6(8)9/h4-5H,3,7H2,1-2H3,(H,8,9)/t4-,5-/m0/s1 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| CAS number: | 73-32-5 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| IUPAC Name: | (2S,3S)-2-amino-3-methylpentanoic acid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Traditional IUPAC Name: | L-isoleucine | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| SMILES: | CC[C@H](C)[C@H](N)C(O)=O | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Chemical Taxonomy | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Description | belongs to the class of organic compounds known as isoleucine and derivatives. Isoleucine and derivatives are compounds containing isoleucine or a derivative thereof resulting from reaction of isoleucine 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 | Isoleucine and derivatives | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Alternative Parents | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Substituents |
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| Molecular Framework | Aliphatic acyclic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| External Descriptors |
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| Physical Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| State: | Solid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Charge: | 0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Melting point: | 285.5 °C | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Experimental Properties: |
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| Predicted Properties |
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| Biological Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Cellular Locations: | Cytoplasm | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Reactions: | Adenosine triphosphate + Water + L-Isoleucine > ADP + Hydrogen ion + L-Isoleucine + Phosphate Adenosine triphosphate + Water + L-Isoleucine > ADP + Hydrogen ion + L-Isoleucine + Phosphate Adenosine triphosphate + L-Isoleucine + tRNA(Ile) + tRNA(Ile) <> Adenosine monophosphate + L-Isoleucyl-tRNA(Ile) + Pyrophosphate + L-Isoleucyl-tRNA(Ile) alpha-Ketoglutarate + L-Isoleucine <> 3-Methyl-2-oxovaleric acid + L-Glutamate Adenosine triphosphate + L-Isoleucine + tRNA(Ile) <> Adenosine monophosphate + Pyrophosphate + L-Isoleucyl-tRNA(Ile) Adenosine triphosphate + L-Isoleucine + Water > ADP + Phosphate + L-Isoleucine + Hydrogen ion Adenosine triphosphate + L-Isoleucine + Water > ADP + Phosphate + L-Isoleucine + Hydrogen ion L-Isoleucine + Oxoglutaric acid <> 3-Methyl-2-oxovaleric acid + L-Glutamate L-Isoleucine + Oxoglutaric acid > (S)-3-methyl-2-oxopentanoate + L-Glutamate Adenosine triphosphate + L-Isoleucine + tRNA(Ile) > Adenosine monophosphate + Pyrophosphate + L-isoleucyl-tRNA(Ile) L-Isoleucine + Adenosine triphosphate + Hydrogen ion + tRNA(Ile) + L-Isoleucine > L-Isoleucyl-tRNA(Ile) + Adenosine monophosphate + Pyrophosphate 3-Methyl-2-oxovaleric acid + L-Glutamic acid + 3-Methyl-2-oxovaleric acid + L-Glutamate > Oxoglutaric acid + L-Isoleucine + L-Isoleucine L-Isoleucine + Adenosine triphosphate + Water + L-Isoleucine > L-Isoleucine + Adenosine diphosphate + Phosphate + Hydrogen ion + ADP Adenosine triphosphate + L-Isoleucine + tRNA(Ile) <> Adenosine monophosphate + L-Isoleucyl-tRNA(Ile) + Pyrophosphate alpha-Ketoglutarate + L-Isoleucine <>3 3-Methyl-2-oxovaleric acid + L-Glutamate Adenosine triphosphate + L-Isoleucine + tRNA(Ile) <> Adenosine monophosphate + L-Isoleucyl-tRNA(Ile) + Pyrophosphate | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| 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: | Marvel, C. S. L-Isoleucine. Organic Syntheses (1941), 21 60-4. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Material Safety Data Sheet (MSDS) | Download (PDF) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Links | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| External Links: |
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Enzymes
- General function:
- Involved in nucleotide binding
- Specific function:
- Catalyzes the attachment of isoleucine to tRNA(Ile). As IleRS can inadvertently accommodate and process structurally similar amino acids such as valine, to avoid such errors it has two additional distinct tRNA(Ile)-dependent editing activities. One activity is designated as 'pretransfer' editing and involves the hydrolysis of activated Val-AMP. The other activity is designated 'posttransfer' editing and involves deacylation of mischarged Val-tRNA(Ile)
- Gene Name:
- ileS
- Uniprot ID:
- P00956
- Molecular weight:
- 104296
Reactions
| ATP + L-isoleucine + tRNA(Ile) = AMP + diphosphate + L-isoleucyl-tRNA(Ile). |
- General function:
- Involved in transporter activity
- Specific function:
- Part of the binding-protein-dependent transport system for branched-chain amino acids. Probably responsible for the translocation of the substrates across the membrane
- Gene Name:
- livH
- Uniprot ID:
- P0AEX7
- Molecular weight:
- 32982
- General function:
- Involved in transporter activity
- Specific function:
- Part of the binding-protein-dependent transport system for branched-chain amino acids. Probably responsible for the translocation of the substrates across the membrane
- Gene Name:
- livM
- Uniprot ID:
- P22729
- Molecular weight:
- 46269
- General function:
- Involved in catalytic activity
- Specific function:
- Acts on leucine, isoleucine and valine
- Gene Name:
- ilvE
- Uniprot ID:
- P0AB80
- Molecular weight:
- 34093
Reactions
| L-leucine + 2-oxoglutarate = 4-methyl-2-oxopentanoate + L-glutamate. |
| L-isoleucine + 2-oxoglutarate = (S)-3-methyl-2-oxopentanoate + L-glutamate. |
| L-valine + 2-oxoglutarate = 3-methyl-2-oxobutanoate + L-glutamate. |
- General function:
- Involved in nucleotide binding
- Specific function:
- Component of the leucine-specific transport system
- Gene Name:
- livG
- Uniprot ID:
- P0A9S7
- Molecular weight:
- 28427
- General function:
- Involved in amino acid transport
- Specific function:
- This protein is a component of the leucine, isoleucine, valine, (threonine) transport system, which is one of the two periplasmic binding protein-dependent transport systems of the high-affinity transport of the branched-chain amino acids
- Gene Name:
- livJ
- Uniprot ID:
- P0AD96
- Molecular weight:
- 39076
- General function:
- Involved in nucleotide binding
- Specific function:
- Component of the leucine-specific transport system
- Gene Name:
- livF
- Uniprot ID:
- P22731
- Molecular weight:
- 26310
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 transporter activity
- Specific function:
- Part of the binding-protein-dependent transport system for branched-chain amino acids. Probably responsible for the translocation of the substrates across the membrane
- Gene Name:
- livH
- Uniprot ID:
- P0AEX7
- Molecular weight:
- 32982
- General function:
- Involved in transporter activity
- Specific function:
- Part of the binding-protein-dependent transport system for branched-chain amino acids. Probably responsible for the translocation of the substrates across the membrane
- Gene Name:
- livM
- Uniprot ID:
- P22729
- Molecular weight:
- 46269
- General function:
- Involved in transporter activity
- Specific function:
- Non-specific porin
- Gene Name:
- ompN
- Uniprot ID:
- P77747
- Molecular weight:
- 41220
- 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 nucleotide binding
- Specific function:
- Component of the leucine-specific transport system
- Gene Name:
- livG
- Uniprot ID:
- P0A9S7
- Molecular weight:
- 28427
- General function:
- Involved in amino acid transport
- Specific function:
- This protein is a component of the leucine, isoleucine, valine, (threonine) transport system, which is one of the two periplasmic binding protein-dependent transport systems of the high-affinity transport of the branched-chain amino acids
- Gene Name:
- livJ
- Uniprot ID:
- P0AD96
- Molecular weight:
- 39076
- General function:
- Involved in nucleotide binding
- Specific function:
- Component of the leucine-specific transport system
- Gene Name:
- livF
- Uniprot ID:
- P22731
- Molecular weight:
- 26310
- 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 branched-chain aliphatic amino acid transmembrane transporter activity
- Specific function:
- Component of the LIV-II transport system for branched- chain amino acids. This LIV-II transport system may be H(+)- coupled
- Gene Name:
- brnQ
- Uniprot ID:
- P0AD99
- Molecular weight:
- 46208
- 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