L-Cystathionine (ECMDB00099) (M2MDB000038)
| Record Information | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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| Version | 2.0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Creation Date | 2012-05-31 09:57:21 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Update Date | 2015-09-13 12:56:06 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Secondary Accession Numbers |
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| Identification | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Name: | L-Cystathionine | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Description | Cystathionine is an intermediate in the synthesis of cysteine. It is generated from homocysteine and serine by cystathionine beta synthase. It is cleaved into cysteine and ketobutyrate by cystathionine gamma-lyase. (Wikipedia) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Structure |  | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Synonyms: |
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| Chemical Formula: | C7H14N2O4S | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Weight: | Average: 222.262 Monoisotopic: 222.067427636 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| InChI Key: | ILRYLPWNYFXEMH-WHFBIAKZSA-N | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| InChI: | InChI=1S/C7H14N2O4S/c8-4(6(10)11)1-2-14-3-5(9)7(12)13/h4-5H,1-3,8-9H2,(H,10,11)(H,12,13)/t4-,5-/m0/s1 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| CAS number: | 56-88-2 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| IUPAC Name: | (2S)-2-amino-4-{[(2R)-2-amino-2-carboxyethyl]sulfanyl}butanoic acid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Traditional IUPAC Name: | L-cystathionine | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| SMILES: | N[C@@H](CCSC[C@H](N)C(O)=O)C(O)=O | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Chemical Taxonomy | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Description | belongs to the class of organic compounds known as l-cysteine-s-conjugates. L-cysteine-S-conjugates are compounds containing L-cysteine where the thio-group is conjugated. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Kingdom | Organic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Super Class | Organic acids and derivatives | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Class | Carboxylic acids and derivatives | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Sub Class | Amino acids, peptides, and analogues | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Direct Parent | L-cysteine-S-conjugates | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| 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: | 312 °C | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Experimental Properties: |
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| Predicted Properties |
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| Biological Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Cellular Locations: | Cytoplasm | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Reactions: | L-Cystathionine + Water > L-Homocysteine + Ammonium + Pyruvic acid L-Cysteine + O-Succinyl-L-homoserine <> L-Cystathionine + Hydrogen ion + Succinic acid L-Cystathionine + Water <> L-Homocysteine + Ammonia + Pyruvic acid o-acetyl-l-homoserine + L-Cysteine <> L-Cystathionine + Acetic acid O-Succinyl-L-homoserine + L-Cysteine <> L-Cystathionine + Succinic acid L-Cystathionine + Water > Hydrogen ion + Pyruvic acid + Ammonia + L-Homocysteine L-Cysteine + O-Succinyl-L-homoserine > Hydrogen ion + Succinic acid + L-Cystathionine L-Cystathionine + Water > L-Homocysteine + Ammonia + Pyruvic acid O-Succinyl-L-homoserine + L-Cysteine > L-Cystathionine + Succinic acid L-Cystathionine + Water + 2-Aminoacrylic acid + 2-Iminopropanoate <> L-Homocysteine + Pyruvic acid + Ammonia L-Cystathionine > Hydrogen ion + Homocysteine + 2-aminoprop-2-enoate + Homocysteine | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| SMPDB Pathways: |
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| KEGG Pathways: | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| EcoCyc Pathways: |
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| Concentrations | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Spectra | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Spectra: | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| References | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| References: |
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| Synthesis Reference: | Yamagata, Shuzo; Akamatsu, Tsuyoshi; Iwama, Tomonori. Immobilization of Saccharomyces cerevisiae cystathionine gamma-lyase and application of the product to cystathionine synthesis. Applied and Environmental Microbiology (2004), 70(6), 3766-3768. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Material Safety Data Sheet (MSDS) | Download (PDF) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Links | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| External Links: |
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Enzymes
- General function:
- Involved in pyridoxal phosphate binding
- Specific function:
- O(4)-succinyl-L-homoserine + L-cysteine = L- cystathionine + succinate
- Gene Name:
- metB
- Uniprot ID:
- P00935
- Molecular weight:
- 41550
Reactions
| O(4)-succinyl-L-homoserine + L-cysteine = L-cystathionine + succinate. |
- General function:
- Involved in pyridoxal phosphate binding
- Specific function:
- L-cystathionine + H(2)O = L-homocysteine + NH(3) + pyruvate
- Gene Name:
- metC
- Uniprot ID:
- P06721
- Molecular weight:
- 43212
Reactions
| L-cystathionine + H(2)O = L-homocysteine + NH(3) + pyruvate. |
- General function:
- Involved in transferase activity
- Specific function:
- Acts as a beta-cystathionase and as a repressor of the maltose regulon
- Gene Name:
- malY
- Uniprot ID:
- P23256
- Molecular weight:
- 43641
Reactions
| L-cystathionine + H(2)O = L-homocysteine + NH(3) + pyruvate. |
- General function:
- Involved in transporter activity
- Specific function:
- Part of the binding-protein-dependent transport system for dipeptides; probably responsible for the translocation of the substrate across the membrane
- Gene Name:
- dppB
- Uniprot ID:
- P0AEF8
- Molecular weight:
- 37497
- General function:
- Involved in transporter activity
- Specific function:
- Part of the binding-protein-dependent transport system for dipeptides; probably responsible for the translocation of the substrate across the membrane
- Gene Name:
- dppC
- Uniprot ID:
- P0AEG1
- Molecular weight:
- 32308
- General function:
- Involved in transporter activity
- Specific function:
- Part of the binding-protein-dependent transport system for oligopeptides; probably responsible for the translocation of the substrate across the membrane
- Gene Name:
- oppB
- Uniprot ID:
- P0AFH2
- Molecular weight:
- 33443
- General function:
- Involved in transporter activity
- Specific function:
- Part of the binding-protein-dependent transport system for oligopeptides; probably responsible for the translocation of the substrate across the membrane
- Gene Name:
- oppC
- Uniprot ID:
- P0AFH6
- Molecular weight:
- 33022
Transporters
- General function:
- Involved in transporter activity
- Specific function:
- Part of the binding-protein-dependent transport system for dipeptides; probably responsible for the translocation of the substrate across the membrane
- Gene Name:
- dppB
- Uniprot ID:
- P0AEF8
- Molecular weight:
- 37497
- General function:
- Involved in transporter activity
- Specific function:
- Part of the binding-protein-dependent transport system for dipeptides; probably responsible for the translocation of the substrate across the membrane
- Gene Name:
- dppC
- Uniprot ID:
- P0AEG1
- Molecular weight:
- 32308
- General function:
- Involved in transporter activity
- Specific function:
- Part of the binding-protein-dependent transport system for oligopeptides; probably responsible for the translocation of the substrate across the membrane
- Gene Name:
- oppB
- Uniprot ID:
- P0AFH2
- Molecular weight:
- 33443
- General function:
- Involved in transporter activity
- Specific function:
- Part of the binding-protein-dependent transport system for oligopeptides; probably responsible for the translocation of the substrate across the membrane
- Gene Name:
- oppC
- Uniprot ID:
- P0AFH6
- Molecular weight:
- 33022
- General function:
- Involved in transporter activity
- Specific function:
- Involved in a peptide intake transport system that plays a role in the resistance to antimicrobial peptides
- Gene Name:
- sapB
- Uniprot ID:
- P0AGH3
- Molecular weight:
- 36038
- General function:
- Involved in transporter activity
- Specific function:
- Involved in a peptide intake transport system that plays a role in the resistance to antimicrobial peptides
- Gene Name:
- sapC
- Uniprot ID:
- P0AGH5
- Molecular weight:
- 31548
- General function:
- Involved in peptide transporter activity
- Specific function:
- Proton-dependent permease that transports di- and tripeptides. Has a clear preference for dipeptides and tripeptides composed of L-amino acids, and discriminates dipeptides on the basis of the position of charges within the substrate
- Gene Name:
- dtpB
- Uniprot ID:
- P36837
- Molecular weight:
- 53575
- General function:
- Involved in peptide transporter activity
- Specific function:
- Probable proton-dependent permease that transports di- and tripeptides. Shows significantly higher specificity towards dipeptides
- Gene Name:
- yjdL
- Uniprot ID:
- P39276
- Molecular weight:
- 53054
- General function:
- Involved in peptide transporter activity
- Specific function:
- Probable proton-dependent permease that transports dipeptides
- Gene Name:
- dtpD
- Uniprot ID:
- P75742
- Molecular weight:
- 54158
- General function:
- Involved in peptide transporter activity
- Specific function:
- Proton-dependent permease that transports di- and tripeptides as well as structurally related peptidomimetics such as aminocephalosporins into the cell. Has a clear preference for dipeptides and tripeptides composed of L-amino acids, and discriminates dipeptides on the basis of the position of charges within the substrate
- Gene Name:
- dtpA
- Uniprot ID:
- P77304
- Molecular weight:
- 53991