L-Lysine (ECMDB00182) (M2MDB000075)
| Record Information | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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| Version | 2.0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Creation Date | 2012-05-31 10:23:06 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Update Date | 2015-09-13 12:56:06 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Secondary Accession Numbers |
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| Identification | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Name: | L-Lysine | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Description | L-lysine is an alpha-amino acid with the chemical formula HO2CCH(NH2)(CH2)4NH2. Lysine is a basic amino acid as are arginine and histidine. Lysine is a proteogenic amino acid, meaning that it is used in protein synthesis. Lysine typically constitutes about 7-8% of an average protein. The epsilon-amino group often participates in hydrogen bonding and as a general base in catalysis. Common posttranslational modifications include methylation of the epsilon-amino group, giving methyl-, dimethyl-, and trimethyllysine. In bacteria, lysine is synthesized from aspartic acid, which is first converted to aspartyl-semialdehyde. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Structure |  | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Synonyms: |
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| Chemical Formula: | C6H14N2O2 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Weight: | Average: 146.1876 Monoisotopic: 146.105527702 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| InChI Key: | KDXKERNSBIXSRK-YFKPBYRVSA-N | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| InChI: | InChI=1S/C6H14N2O2/c7-4-2-1-3-5(8)6(9)10/h5H,1-4,7-8H2,(H,9,10)/t5-/m0/s1 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| CAS number: | 56-87-1 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| IUPAC Name: | (2S)-2,6-diaminohexanoic acid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Traditional IUPAC Name: | L-lysine | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| SMILES: | NCCCC[C@H](N)C(O)=O | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Chemical Taxonomy | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Description | 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: | 1 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Melting point: | 224.5 °C | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Experimental Properties: |
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| Predicted Properties |
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| Biological Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Cellular Locations: | Cytoplasm | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Reactions: | Hydrogen ion + L-Lysine <> Cadaverine + Carbon dioxide Adenosine triphosphate + Water + L-Lysine > ADP + Hydrogen ion + L-Lysine + Phosphate Adenosine triphosphate + Water + L-Lysine > ADP + Hydrogen ion + L-Lysine + Phosphate Adenosine triphosphate + L-Lysine + tRNA(Lys) > Adenosine monophosphate + L-Lysine-tRNA (Lys) + Pyrophosphate Diaminopimelic acid + Hydrogen ion > Carbon dioxide + L-Lysine Fructoselysine-6-phosphate + Water <> Glucose 6-phosphate + L-Lysine Meso-2,6-Diaminoheptanedioate <> L-Lysine + Carbon dioxide L-Lysine <> Cadaverine + Carbon dioxide Adenosine triphosphate + L-Lysine + tRNA(Lys) + tRNA(Lys) <> Adenosine monophosphate + Pyrophosphate + L-Lysyl-tRNA + L-Lysyl-tRNA [tRNA(Ile2)]-cytidine34 + L-Lysine + Adenosine triphosphate <> [tRNA(Ile2)]-lysidine34 + Adenosine monophosphate + Pyrophosphate + Water L-Lysine + Adenosine triphosphate + Water > L-Lysine + ADP + Phosphate + Hydrogen ion L-Lysine + Adenosine triphosphate + Water > L-Lysine + ADP + Phosphate + Hydrogen ion Hydrogen ion + <i>meso</i>-diaminopimelate > L-Lysine + Carbon dioxide Hydrogen ion + L-Lysine > Carbon dioxide + Cadaverine L-Lysine (R)-beta-lysine Meso-2,6-Diaminoheptanedioate > L-Lysine + Carbon dioxide L-Lysine > Cadaverine + Carbon dioxide L-Lysine > (R)-beta-lysine Fructoselysine-6-phosphate + Water > Glucose 6-phosphate + L-Lysine Adenosine triphosphate + L-Lysine + tRNA(Lys) > Adenosine monophosphate + Pyrophosphate + L-lysyl-tRNA(Lys) (tRNA(Ile2))-cytidine(34) + L-Lysine + Adenosine triphosphate > (tRNA(Ile2))-lysidine(34) + Adenosine monophosphate + Pyrophosphate + Water Biocytin + Water > Biotin + L-Lysine + L-Lysine Meso-2,6-Diaminoheptanedioate + Hydrogen ion > L-Lysine + Carbon dioxide + L-Lysine L-Lysine + Hydrogen ion + L-Lysine > Cadaverine + Carbon dioxide L-Lysine + L-Lysine > Cadaverine L-Lysine + Adenosine triphosphate + Hydrogen ion + tRNA(Lys) + L-Lysine > Adenosine monophosphate + Pyrophosphate + L-Lysyl-tRNA More...L-Lysine + Adenosine triphosphate + Water + L-Lysine > Adenosine diphosphate + Phosphate + Hydrogen ion + L-Lysine + ADP Fructoselysine-6-phosphate + Water <> β-D-glucose 6-phosphate + L-Lysine Adenosine triphosphate + L-Lysine + tRNA(Lys) <> Adenosine monophosphate + Pyrophosphate + L-Lysyl-tRNA Meso-2,6-Diaminoheptanedioate <> L-Lysine + Carbon dioxide Adenosine triphosphate + L-Lysine + tRNA(Lys) <> Adenosine monophosphate + Pyrophosphate + L-Lysyl-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: | Rothstein, Morton. DL-Lysine-6-C14 and DL-a-aminoadipic acid-6-C14. Biochemical Preparations (1961), 8 85-8. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Material Safety Data Sheet (MSDS) | Download (PDF) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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| External Links: |
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Enzymes
- General function:
- Involved in catalytic activity
- Specific function:
- Meso-2,6-diaminoheptanedioate = L-lysine + CO(2)
- Gene Name:
- lysA
- Uniprot ID:
- P00861
- Molecular weight:
- 46177
Reactions
| Meso-2,6-diaminoheptanedioate = L-lysine + CO(2). |
- General function:
- Involved in nucleotide binding
- Specific function:
- Part of the binding-protein-dependent transport system for histidine. Probably responsible for energy coupling to the transport system
- Gene Name:
- hisP
- Uniprot ID:
- P07109
- Molecular weight:
- 28653
- General function:
- Involved in nucleotide binding
- Specific function:
- ATP + L-lysine + tRNA(Lys) = AMP + diphosphate + L-lysyl-tRNA(Lys)
- Gene Name:
- lysS
- Uniprot ID:
- P0A8N3
- Molecular weight:
- 57603
Reactions
| ATP + L-lysine + tRNA(Lys) = AMP + diphosphate + L-lysyl-tRNA(Lys). |
- General function:
- Involved in nucleotide binding
- Specific function:
- Also can synthesize a number of adenyl dinucleotides (in particular AppppA). These dinucleotides have been proposed to act as modulators of the heat-shock response and stress response
- Gene Name:
- lysU
- Uniprot ID:
- P0A8N5
- Molecular weight:
- 57826
Reactions
| ATP + L-lysine + tRNA(Lys) = AMP + diphosphate + L-lysyl-tRNA(Lys). |
- General function:
- Involved in nucleotide binding
- Specific function:
- With YjeK might be involved in the post-translational modification of elongation factor P (EF-P)
- Gene Name:
- poxA
- Uniprot ID:
- P0A8N7
- Molecular weight:
- 36976
- General function:
- Involved in carboxy-lyase activity
- Specific function:
- Appears to play a role in pH homeostasis by consuming protons and neutralizing the acidic by-products of carbohydrate fermentation
- Gene Name:
- cadA
- Uniprot ID:
- P0A9H3
- Molecular weight:
- 81260
Reactions
| L-lysine = cadaverine + CO(2). |
- General function:
- Involved in carbohydrate binding
- Specific function:
- Catalyzes the conversion of fructoselysine 6-phosphate to glucose 6-phosphate and lysine
- Gene Name:
- frlB
- Uniprot ID:
- P0AC00
- Molecular weight:
- 38569
Reactions
| Fructoselysine 6-phosphate + H(2)O = glucose 6-phosphate + L-lysine. |
- General function:
- Involved in carboxy-lyase activity
- Specific function:
- LDC is constitutively but weakly expressed under various conditions
- Gene Name:
- ldcC
- Uniprot ID:
- P52095
- Molecular weight:
- 80590
Reactions
| L-lysine = cadaverine + CO(2). |
- General function:
- Involved in transporter activity
- Specific function:
- Part of the binding-protein-dependent transport system for histidine; probably responsible for the translocation of the substrate across the membrane
- Gene Name:
- hisM
- Uniprot ID:
- P0AEU3
- Molecular weight:
- 26870
- General function:
- Involved in transporter activity
- Specific function:
- Part of the binding-protein-dependent transport system for histidine; probably responsible for the translocation of the substrate across the membrane
- Gene Name:
- hisQ
- Uniprot ID:
- P52094
- Molecular weight:
- 24649
- General function:
- Involved in transporter activity
- Specific function:
- This periplasmic binding protein is involved in an arginine transport system. ArgT and histidine-binding protein J (hisJ) interact with a common membrane-bound receptor, hisP
- Gene Name:
- argT
- Uniprot ID:
- P09551
- Molecular weight:
- 27991
- General function:
- Not Available
- Specific function:
- Not Available
- Gene Name:
- tilS
- Uniprot ID:
- P52097
- Molecular weight:
- Not Available
Transporters
- General function:
- Involved in nucleotide binding
- Specific function:
- Part of the binding-protein-dependent transport system for histidine. Probably responsible for energy coupling to the transport system
- Gene Name:
- hisP
- Uniprot ID:
- P07109
- Molecular weight:
- 28653
- 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 histidine; probably responsible for the translocation of the substrate across the membrane
- Gene Name:
- hisM
- Uniprot ID:
- P0AEU3
- Molecular weight:
- 26870
- General function:
- Involved in transport
- Specific function:
- Permease that is involved in the transport across the cytoplasmic membrane of lysine
- Gene Name:
- lysP
- Uniprot ID:
- P25737
- Molecular weight:
- 53575
- General function:
- Involved in transporter activity
- Specific function:
- Part of the binding-protein-dependent transport system for histidine; probably responsible for the translocation of the substrate across the membrane
- Gene Name:
- hisQ
- Uniprot ID:
- P52094
- Molecular weight:
- 24649
- General function:
- Involved in transporter activity
- Specific function:
- This periplasmic binding protein is involved in an arginine transport system. ArgT and histidine-binding protein J (hisJ) interact with a common membrane-bound receptor, hisP
- Gene Name:
- argT
- Uniprot ID:
- P09551
- Molecular weight:
- 27991
- 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 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 amino acid transmembrane transporter activity
- Specific function:
- Probable cadaverine/lysine antiporter or part of it
- Gene Name:
- cadB
- Uniprot ID:
- P0AAE8
- Molecular weight:
- 46665
- General function:
- Involved in amino acid transport
- Specific function:
- Involved in the export of arginine. Important to control the intracellular level of arginine and the correct balance between arginine and lysine. May also be involved in the export of canavanine (a plant-derived antimetabolite)
- Gene Name:
- argO
- Uniprot ID:
- P11667
- Molecular weight:
- 23175
- 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