L-Leucine (PAMDB000170)
| Record Information | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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| Version | 1.0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Update Date | 1/22/2018 12:54:54 PM | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Metabolite ID | PAMDB000170 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| 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 |
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| Synonyms: |
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| Chemical Formula: | C6H13NO2 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Average Molecular Weight: | 131.1729 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Monoisotopic Molecular Weight: | 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 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Taxonomy Description | This compound belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Kingdom | Organic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Super Class | Organic acids and derivatives | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Class | Carboxylic acids and derivatives | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Sub Class | Amino acids, peptides, and analogues | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Direct Parent | L-alpha-amino acids | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| 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 -->-->L-Leucine + Oxoglutaric acid <> Ketoleucine + L-Glutamate ala-leu + Water > L-Alanine + L-Leucine 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 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Pathways: | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| 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
- Locus Tag:
- PA3139
- Molecular weight:
- 43.3 kDa
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
- Locus Tag:
- PA3987
- Molecular weight:
- 97.6 kDa
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
- Locus Tag:
- PA1073
- Molecular weight:
- 32.5 kDa
- 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
- Locus Tag:
- PA1072
- Molecular weight:
- 45.6 kDa
- General function:
- Involved in catalytic activity
- Specific function:
- Acts on leucine, isoleucine and valine
- Gene Name:
- ilvE
- Locus Tag:
- PA5013
- Molecular weight:
- 34.1 kDa
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
- Locus Tag:
- PA1071
- Molecular weight:
- 28.3 kDa
- General function:
- Involved in nucleotide binding
- Specific function:
- Component of the leucine-specific transport system
- Gene Name:
- livF
- Locus Tag:
- PA1070
- Molecular weight:
- 25.6 kDa
- 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 Pseudomonas aeruginosa
- Gene Name:
- livK
- Locus Tag:
- PA1074
- Molecular weight:
- 39.8 kDa
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
- Locus Tag:
- PA5152
- Molecular weight:
- 28.4 kDa
- 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
- Locus Tag:
- PA1073
- Molecular weight:
- 32.5 kDa
- 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
- Locus Tag:
- PA1072
- Molecular weight:
- 45.6 kDa
- General function:
- Involved in nucleotide binding
- Specific function:
- Component of the leucine-specific transport system
- Gene Name:
- livG
- Locus Tag:
- PA1071
- Molecular weight:
- 28.3 kDa
- General function:
- Involved in nucleotide binding
- Specific function:
- Component of the leucine-specific transport system
- Gene Name:
- livF
- Locus Tag:
- PA1070
- Molecular weight:
- 25.6 kDa
- 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
- Locus Tag:
- PA1971
- Molecular weight:
- 45.3 kDa
- 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 Pseudomonas aeruginosa
- Gene Name:
- livK
- Locus Tag:
- PA1074
- Molecular weight:
- 39.8 kDa