L-Alanine-D-glutamate-meso-2,6-diaminoheptanedioate-D-alanine (ECMDB21239) (M2MDB001647)
Record Information | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
Version | 2.0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Creation Date | 2012-07-30 14:55:05 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Update Date | 2015-06-03 17:20:58 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Secondary Accession Numbers |
| ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Identification | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Name: | L-Alanine-D-glutamate-meso-2,6-diaminoheptanedioate-D-alanine | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Description | L-alanine-d-glutamate-meso-2,6-diaminoheptanedioate-d-alanine belongs to the class of Peptides. These are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another. (inferred from compound structure) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Structure | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Synonyms: |
| ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Chemical Formula: | C18H31N5O9 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Weight: | Average: 461.4668 Monoisotopic: 461.212177615 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
InChI Key: | BAPAFFOXTCMVCC-UHFFFAOYSA-N | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
InChI: | InChI=1S/C18H31N5O9/c1-8(19)14(25)22-11(17(29)30)5-3-4-10(16(27)28)21-13(24)7-6-12(18(31)32)23-15(26)9(2)20/h8-12H,3-7,19-20H2,1-2H3,(H,21,24)(H,22,25)(H,23,26)(H,27,28)(H,29,30)(H,31,32) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
CAS number: | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
IUPAC Name: | 2-[(2-amino-1-hydroxypropylidene)amino]-6-({4-[(2-amino-1-hydroxypropylidene)amino]-4-carboxy-1-hydroxybutylidene}amino)heptanedioic acid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Traditional IUPAC Name: | 2-[(2-amino-1-hydroxypropylidene)amino]-6-({4-[(2-amino-1-hydroxypropylidene)amino]-4-carboxy-1-hydroxybutylidene}amino)heptanedioic acid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
SMILES: | CC(N)C(O)=NC(CCCC(N=C(O)CCC(N=C(O)C(C)N)C(O)=O)C(O)=O)C(O)=O | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Chemical Taxonomy | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Description | belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Kingdom | Organic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Super Class | Organic acids and derivatives | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Class | Carboxylic acids and derivatives | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Sub Class | Amino acids, peptides, and analogues | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Direct Parent | Dipeptides | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Alternative Parents |
| ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Substituents |
| ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Molecular Framework | Aliphatic acyclic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
External Descriptors | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Physical Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
State: | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Charge: | 0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Melting point: | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Experimental Properties: |
| ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Predicted Properties |
| ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Biological Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Cellular Locations: | Cytoplasm | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Reactions: | Adenosine triphosphate + Water + L-Alanine-D-glutamate-meso-2,6-diaminoheptanedioate-D-alanine > L-Alanine-D-glutamate-meso-2,6-diaminoheptanedioate-D-alanine + ADP + Hydrogen ion + Phosphate Adenosine triphosphate + Water + L-Alanine-D-glutamate-meso-2,6-diaminoheptanedioate-D-alanine > L-Alanine-D-glutamate-meso-2,6-diaminoheptanedioate-D-alanine + ADP + Hydrogen ion + Phosphate N-Acetyl-D-glucosamine(anhydrous)N-Acetylmuramyl-tetrapeptide + Water > L-Alanine-D-glutamate-meso-2,6-diaminoheptanedioate-D-alanine + N-Acetyl-D-glucosamine(anhydrous)N-Acetylmuramic acid 1,6-Anhydrous-N-Acetylmuramyl-tetrapeptide + Water > L-Alanine-D-glutamate-meso-2,6-diaminoheptanedioate-D-alanine + 1,6-Anhydro-N-acetylmuramate L-Alanine-D-glutamate-meso-2,6-diaminoheptanedioate-D-alanine + Water > L-alanine-D-glutamate-meso-2,6-diaminoheptanedioate + D-Alanine L-Alanine-D-glutamate-meso-2,6-diaminoheptanedioate-D-alanine + Adenosine triphosphate + UDP-N-Acetylmuraminate > ADP + Hydrogen ion + Phosphate + UDP-N-acetylmuramoyl-L-alanyl-D-gamma-glutamyl-meso-2,6-diaminopimelate-D-alanine | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
SMPDB Pathways: | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
KEGG Pathways: | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
EcoCyc Pathways: | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Concentrations | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra: | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
References | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
References: | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Synthesis Reference: | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Material Safety Data Sheet (MSDS) | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Links | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
External Links: |
|
Enzymes
- General function:
- Involved in N-acetylmuramoyl-L-alanine amidase activity
- Specific function:
- Cell-wall hydrolase probably involved in cell-wall hydrolysis, septation or recycling
- Gene Name:
- amiB
- Uniprot ID:
- P26365
- Molecular weight:
- 47985
Reactions
Hydrolyzes the link between N-acetylmuramoyl residues and L-amino acid residues in certain cell-wall glycopeptides. |
- General function:
- Involved in N-acetylmuramoyl-L-alanine amidase activity
- Specific function:
- Hydrolyzes the link between N-acetylmuramoyl residues and L-amino acid residues in certain cell-wall glycopeptides
- Gene Name:
- amiA
- Uniprot ID:
- P36548
- Molecular weight:
- 31412
Reactions
Hydrolyzes the link between N-acetylmuramoyl residues and L-amino acid residues in certain cell-wall glycopeptides. |
- General function:
- Involved in N-acetylmuramoyl-L-alanine amidase activity
- Specific function:
- Cell-wall hydrolase probably involved in cell-wall hydrolysis, septation or recycling
- Gene Name:
- amiC
- Uniprot ID:
- P63883
- Molecular weight:
- 45634
Reactions
Hydrolyzes the link between N-acetylmuramoyl residues and L-amino acid residues in certain cell-wall glycopeptides. |
- General function:
- Defense mechanisms
- Specific function:
- Releases the terminal D-alanine residue from the cytoplasmic tetrapeptide recycling product L-Ala-gamma-D-Glu-meso- Dap-D-Ala. To a lesser extent, can also cleave D-Ala from murein derivatives containing the tetrapeptide, i.e. MurNAc-tetrapeptide, UDP-MurNAc-tetrapeptide, GlcNAc-MurNAc-tetrapeptide, and GlcNAc- anhMurNAc-tetrapeptide. Does not act on murein sacculi or cross- linked muropeptides. The tripeptides produced by the lcdA reaction can then be reused as peptidoglycan building blocks; lcdA is thereby involved in murein recycling. Is also essential for viability during stationary phase
- Gene Name:
- ldcA
- Uniprot ID:
- P76008
- Molecular weight:
- 33567
Reactions
GlcNAc-MurNAc-L-alanyl-gamma-D-glutamyl-meso-diaminopimelyl-D-alanine + H(2)O = GlcNAc-MurNAc-L-alanyl-gamma-D-glutamyl-meso-diaminopimelate + D-alanine. |
- 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 nucleotide binding
- Specific function:
- Part of the binding-protein-dependent transport system for oligopeptides. Probably responsible for energy coupling to the transport system
- Gene Name:
- oppF
- Uniprot ID:
- P77737
- Molecular weight:
- 37197
- General function:
- Involved in transporter activity
- Specific function:
- This protein is a component of the oligopeptide permease, a binding protein-dependent transport system, it binds peptides up to five amino acids long with high affinity
- Gene Name:
- oppA
- Uniprot ID:
- P23843
- Molecular weight:
- 60899
- General function:
- Involved in nucleotide binding
- Specific function:
- Part of the binding-protein-dependent transport system for oligopeptides. Probably responsible for energy coupling to the transport system
- Gene Name:
- oppD
- Uniprot ID:
- P76027
- Molecular weight:
- 37188
- General function:
- Involved in N-acetylmuramoyl-L-alanine amidase activity
- Specific function:
- Involved in both cell wall peptidoglycans recycling and beta-lactamase induction. Specifically cleaves the amide bond between the lactyl group of N-acetylmuramic acid and the alpha- amino group of the L-alanine in degradation products containing an anhydro N-acetylmuramyl moiety
- Gene Name:
- ampD
- Uniprot ID:
- P13016
- Molecular weight:
- 20536
Reactions
Hydrolyzes the link between N-acetylmuramoyl residues and L-amino acid residues in certain cell-wall glycopeptides. |
- General function:
- Involved in ATP binding
- Specific function:
- Reutilizes the intact tripeptide L-alanyl-gamma-D- glutamyl-meso-diaminopimelate by linking it to UDP-N-acetylmuramic acid
- Gene Name:
- mpl
- Uniprot ID:
- P37773
- Molecular weight:
- 49874
Transporters
- 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 nucleotide binding
- Specific function:
- Part of the binding-protein-dependent transport system for oligopeptides. Probably responsible for energy coupling to the transport system
- Gene Name:
- oppF
- Uniprot ID:
- P77737
- Molecular weight:
- 37197
- 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:
- This protein is a component of the oligopeptide permease, a binding protein-dependent transport system, it binds peptides up to five amino acids long with high affinity
- Gene Name:
- oppA
- Uniprot ID:
- P23843
- Molecular weight:
- 60899
- 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 nucleotide binding
- Specific function:
- Part of the binding-protein-dependent transport system for oligopeptides. Probably responsible for energy coupling to the transport system
- Gene Name:
- oppD
- Uniprot ID:
- P76027
- Molecular weight:
- 37188
- 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