L-Leucine (ECMDB00687) (M2MDB000170)
| Record Information | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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| Version | 2.0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Creation Date | 2012-05-31 13:00:16 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Update Date | 2015-09-13 12:56:08 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Secondary Accession Numbers |
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| Identification | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Name: | L-Leucine | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Description | Leucine (abbreviated as Leu or L) is an amino acid with the chemical formula HO2CCH(NH2)CH2CH(CH3)2. It is synthesized in plants and microorganisms via several steps starting from pyruvic acid. The initial part of the pathway also leads to valine. The intermediate alpha-ketovalerate is converted to alpha-isopropylmalate and then beta-isopropylmalate, which is dehydrogenated to alpha-ketoisocaproate, which in the final step undergoes reductive amination. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Structure |  | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Synonyms: |
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| Chemical Formula: | C6H13NO2 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Weight: | Average: 131.1729 Monoisotopic: 131.094628665 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| InChI Key: | ROHFNLRQFUQHCH-YFKPBYRVSA-N | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| InChI: | InChI=1S/C6H13NO2/c1-4(2)3-5(7)6(8)9/h4-5H,3,7H2,1-2H3,(H,8,9)/t5-/m0/s1 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| CAS number: | 61-90-5 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| IUPAC Name: | (2S)-2-amino-4-methylpentanoic acid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Traditional IUPAC Name: | L-leucine | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| SMILES: | CC(C)C[C@H](N)C(O)=O | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Chemical Taxonomy | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Description | belongs to the class of organic compounds known as leucine and derivatives. Leucine and derivatives are compounds containing leucine or a derivative thereof resulting from reaction of leucine 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 | Leucine 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: | 268-288 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Experimental Properties: |
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| Predicted Properties |
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| Biological Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Cellular Locations: | Cytoplasm | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Reactions: | Adenosine triphosphate + Water + L-Leucine > ADP + Hydrogen ion + L-Leucine + Phosphate Adenosine triphosphate + Water + L-Leucine > ADP + Hydrogen ion + L-Leucine + Phosphate Ketoleucine + L-Glutamate > alpha-Ketoglutarate + L-Leucine Adenosine triphosphate + L-Leucine + tRNA(Leu) > Adenosine monophosphate + L-Leucyl-tRNA(Leu) + Pyrophosphate L-Leucine + alpha-Ketoglutarate <> 4-Methyl-2-oxopentanoate + L-Glutamate + Ketoleucine Adenosine triphosphate + L-Leucine + tRNA(Leu) + tRNA(Leu) <> Adenosine monophosphate + Pyrophosphate + L-Leucyl-tRNA + L-Leucyl-tRNA Adenosine triphosphate + L-Leucine + Water > ADP + Phosphate + L-Leucine + Hydrogen ion Adenosine triphosphate + L-Leucine + Water > ADP + Phosphate + L-Leucine + Hydrogen ion L-Leucine + Oxoglutaric acid <> Ketoleucine + L-Glutamate ala-leu + Water > L-Alanine + L-Leucine L-Leucine + Oxoglutaric acid > Ketoleucine + L-Glutamate L-Leucine + Adenosine triphosphate + Hydrogen ion + tRNA(Leu) > Adenosine monophosphate + Pyrophosphate + L-Leucyl-tRNA(Leu) Ketoleucine + L-Glutamic acid + L-Glutamate > Oxoglutaric acid + L-Leucine L-Leucine + Adenosine triphosphate + Water > L-Leucine + Adenosine diphosphate + Phosphate + Hydrogen ion + ADP L-Leucine + Adenosine triphosphate + Water > L-Leucine + Adenosine diphosphate + Phosphate + Hydrogen ion + ADP Adenosine triphosphate + L-Leucine + tRNA(Leu) <> Adenosine monophosphate + Pyrophosphate + L-Leucyl-tRNA Adenosine triphosphate + L-Leucine + tRNA(Leu) <> Adenosine monophosphate + Pyrophosphate + L-Leucyl-tRNA | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| 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: | Leuchtenberger, Wolfgang; Karrenbauer, Michael; Ploecker, Ulf. Scale-up of an enzyme membrane reactor process for the manufacture of L-enantiomeric compounds. Annals of the New York Academy of Sciences (1984), 434(Enzyme Eng.), 78-86. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Material Safety Data Sheet (MSDS) | Download (PDF) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Links | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| External Links: |
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Enzymes
- 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 nucleotide binding
- Specific function:
- ATP + L-leucine + tRNA(Leu) = AMP + diphosphate + L-leucyl-tRNA(Leu)
- Gene Name:
- leuS
- Uniprot ID:
- P07813
- Molecular weight:
- 97233
Reactions
| ATP + L-leucine + tRNA(Leu) = AMP + diphosphate + L-leucyl-tRNA(Leu). |
- 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
- General function:
- Involved in amino acid transport
- Specific function:
- This protein is a component of the leucine-specific 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 in E.coli
- Gene Name:
- livK
- Uniprot ID:
- P04816
- Molecular weight:
- 39378
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
- General function:
- Involved in amino acid transport
- Specific function:
- This protein is a component of the leucine-specific 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 in E.coli
- Gene Name:
- livK
- Uniprot ID:
- P04816
- Molecular weight:
- 39378