D-Alanyl-D-alanine (ECMDB03459) (M2MDB000504)
| Record Information | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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| Version | 2.0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Creation Date | 2012-05-31 13:59:16 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Update Date | 2015-09-13 12:56:13 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Secondary Accession Numbers |
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| Identification | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Name: | D-Alanyl-D-alanine | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Description | D-Alanyl-D-alanine is a component of peptidoglycan. The ATP-dependent carboxylate-amine/thiol ligase superfamily is known to contain enzymes catalyzing the formation of various types of peptide, one of which is D-alanyl-D-alanine.(PMID: 16030213) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Structure |  | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Synonyms: |
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| Chemical Formula: | C6H12N2O3 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Weight: | Average: 160.1711 Monoisotopic: 160.08479226 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| InChI Key: | DEFJQIDDEAULHB-QWWZWVQMSA-N | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| InChI: | InChI=1S/C6H12N2O3/c1-3(7)5(9)8-4(2)6(10)11/h3-4H,7H2,1-2H3,(H,8,9)(H,10,11)/t3-,4-/m1/s1 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| CAS number: | 923-16-0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| IUPAC Name: | (2R)-2-[(2R)-2-aminopropanamido]propanoic acid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Traditional IUPAC Name: | D-ala-D-ala | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| SMILES: | C[C@@H](N)C(=O)N[C@H](C)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 |
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| Molecular Framework | Aliphatic acyclic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| External Descriptors |
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| Physical Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| State: | Solid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Charge: | 0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Melting point: | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Experimental Properties: |
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| Predicted Properties |
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| Biological Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Cellular Locations: | Cytoplasm | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Reactions: | Adenosine triphosphate + Water + D-Alanyl-D-alanine > ADP + D-Alanyl-D-alanine + Hydrogen ion + Phosphate Adenosine triphosphate + Water + D-Alanyl-D-alanine > ADP + D-Alanyl-D-alanine + Hydrogen ion + Phosphate two linked disacharide pentapeptide murein units (uncrosslinked, middle of chain) > D-Alanyl-D-alanine + two disacharide linked murein units, pentapeptide corsslinked tripeptide (A2pm->A2pm) (middle of chain) 2 D-Alanine + Adenosine triphosphate <> ADP + D-Alanyl-D-alanine + Hydrogen ion + Phosphate D-Alanyl-D-alanine + Adenosine triphosphate + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminoheptanedioate > ADP + Hydrogen ion + Phosphate + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-6-carboxy-L-lysyl-D-alanyl-D-alanine D-Alanyl-D-alanine + Water >2 D-Alanine Adenosine triphosphate + 2 D-Alanine <> ADP + Phosphate + D-Alanyl-D-alanine Adenosine triphosphate + UDP-N-Acetylmuramoyl-L-alanyl-gamma-D-glutamyl-L-lysine + D-Alanyl-D-alanine <> ADP + Phosphate + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-L-lysyl-D-alanyl-D-alanine Adenosine triphosphate + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminoheptanedioate + D-Alanyl-D-alanine <> ADP + Phosphate + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-6-carboxy-L-lysyl-D-alanyl-D-alanine D-Alanyl-D-alanine + Water > D-Alanine D-Alanine + Adenosine triphosphate > Hydrogen ion + D-Alanyl-D-alanine + Phosphate + ADP Adenosine triphosphate + 2 D-Alanine > ADP + Inorganic phosphate + D-Alanyl-D-alanine Adenosine triphosphate + UDP-N-Acetylmuramoyl-L-alanyl-gamma-D-glutamyl-L-lysine + D-Alanyl-D-alanine > ADP + Inorganic phosphate + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-L-lysyl-D-alanyl-D-alanine D-Alanyl-D-alanine + Water <> D-Alanine 2 D-Alanine + Adenosine triphosphate > D-Alanyl-D-alanine + Adenosine diphosphate + Phosphate + ADP UDP-N-Acetylmuramoyl-L-alanyl-D-gamma-glutamyl-meso-2,6-diaminopimelate + D-Alanyl-D-alanine + Adenosine triphosphate > Adenosine diphosphate + Phosphate + Hydrogen ion + UDP-N-acetyl-α-D-muramoyl-L-alanyl-γ-D-glutamyl-meso-2,6-diaminopimeloyl-D-alanyl-D-alanine + ADP UDP-N-Acetylmuramoyl-L-alanyl-D-gamma-glutamyl-meso-2,6-diaminopimelate + D-Alanyl-D-alanine + Adenosine triphosphate > N-Acetylmuramoyl-L-alanyl-D-glutamyl-L-lysyl-D-alanyl-D-alanine-diphosphoundecaprenyl-N-acetylglucosamine + ADP + Phosphate + Hydrogen ion 2 D-Alanine + Adenosine triphosphate <> ADP + D-Alanyl-D-alanine + Hydrogen ion + Phosphate Adenosine triphosphate + 2 D-Alanine <> ADP + Phosphate + D-Alanyl-D-alanine D-Alanyl-D-alanine + Adenosine triphosphate + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminoheptanedioate > ADP + Hydrogen ion + Phosphate + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-6-carboxy-L-lysyl-D-alanyl-D-alanine 2 D-Alanine + Adenosine triphosphate <> ADP + D-Alanyl-D-alanine + Hydrogen ion + Phosphate D-Alanyl-D-alanine + Adenosine triphosphate + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminoheptanedioate > ADP + Hydrogen ion + Phosphate + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-6-carboxy-L-lysyl-D-alanyl-D-alanine | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| 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: | Neuhaus, Francis C. Enzymic synthesis of D-alanyl-D-alanine. Biochemical and Biophysical Research Communications (1960), 3 401-5. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Material Safety Data Sheet (MSDS) | Download (PDF) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Links | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| External Links: |
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Enzymes
- General function:
- Involved in catalytic activity
- Specific function:
- Cell wall formation. Synthesis of cross-linked peptidoglycan from the lipid intermediates. The enzyme has a penicillin-insensitive transglycosylase N-terminal domain (formation of linear glycan strands) and a penicillin-sensitive transpeptidase C-terminal domain (cross-linking of the peptide subunits)
- Gene Name:
- mrcA
- Uniprot ID:
- P02918
- Molecular weight:
- 93636
- General function:
- Involved in catalytic activity
- Specific function:
- Cell wall formation. Synthesis of cross-linked peptidoglycan from the lipid intermediates. The enzyme has a penicillin-insensitive transglycosylase N-terminal domain (formation of linear glycan strands) and a penicillin-sensitive transpeptidase C-terminal domain (cross-linking of the peptide subunits)
- Gene Name:
- mrcB
- Uniprot ID:
- P02919
- Molecular weight:
- 94292
Reactions
| (GlcNAc-(1->4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala))(n)-diphosphoundecaprenol + GlcNAc-(1->4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol = (GlcNAc-(1->4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala))(n+1)-diphosphoundecaprenol + undecaprenyl diphosphate. |
- General function:
- Involved in ATP binding
- Specific function:
- Cell wall formation
- Gene Name:
- ddlB
- Uniprot ID:
- P07862
- Molecular weight:
- 32839
Reactions
| ATP + 2 D-alanine = ADP + phosphate + D-alanyl-D-alanine. |
- General function:
- Involved in ATP binding
- Specific function:
- Cell wall formation
- Gene Name:
- ddlA
- Uniprot ID:
- P0A6J8
- Molecular weight:
- 39315
Reactions
| ATP + 2 D-alanine = ADP + phosphate + D-alanyl-D-alanine. |
- General function:
- Involved in ATP binding
- Specific function:
- Involved in cell wall formation. Catalyzes the final step in the synthesis of UDP-N-acetylmuramoyl-pentapeptide, the precursor of murein
- Gene Name:
- murF
- Uniprot ID:
- P11880
- Molecular weight:
- 47447
Reactions
| ATP + UDP-N-acetylmuramoyl-L-alanyl-gamma-D-glutamyl-L-lysine + D-alanyl-D-alanine = ADP + phosphate + UDP-N-acetylmuramoyl-L-alanyl-gamma-D-glutamyl-L-lysyl-D-alanyl-D-alanine. |
- 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:
- Part of the ABC transporter complex ddpABCDF, which is probably involved in D,D-dipeptide transport. Probably responsible for the translocation of the substrate across the membrane
- Gene Name:
- ddpB
- Uniprot ID:
- P77308
- Molecular weight:
- 37345
- General function:
- Involved in transporter activity
- Specific function:
- Part of the ABC transporter complex ddpABCDF, which is probably involved in D,D-dipeptide transport. Probably responsible for the translocation of the substrate across the membrane
- Gene Name:
- ddpC
- Uniprot ID:
- P77463
- Molecular weight:
- 31971
- General function:
- Involved in nucleotide binding
- Specific function:
- Part of the ABC transporter complex ddpABCDF, which is probably involved in D,D-dipeptide transport. Probably responsible for energy coupling to the transport system
- Gene Name:
- ddpD
- Uniprot ID:
- P77268
- Molecular weight:
- 36100
- General function:
- Involved in nucleotide binding
- Specific function:
- Part of the binding-protein-dependent transport system for dipeptides. Probably responsible for energy coupling to the transport system
- Gene Name:
- dppD
- Uniprot ID:
- P0AAG0
- Molecular weight:
- 35844
- General function:
- Involved in nucleotide binding
- Specific function:
- Part of the binding-protein-dependent transport system for dipeptides. Probably responsible for energy coupling to the transport system
- Gene Name:
- dppF
- Uniprot ID:
- P37313
- Molecular weight:
- 37560
- General function:
- Involved in nucleotide binding
- Specific function:
- Part of the ABC transporter complex ddpABCDF, which is probably involved in D,D-dipeptide transport. Probably responsible for energy coupling to the transport system
- Gene Name:
- ddpF
- Uniprot ID:
- P77622
- Molecular weight:
- 34621
- General function:
- Involved in transporter activity
- Specific function:
- Dipeptide-binding protein of a transport system that can be subject to osmotic shock. DppA is also required for peptide chemotaxis
- Gene Name:
- dppA
- Uniprot ID:
- P23847
- Molecular weight:
- 60293
- General function:
- Involved in metallopeptidase activity
- Specific function:
- Hydrolyzes D-Ala-D-Ala. May have a role in cell-wall turnover
- Gene Name:
- ddpX
- Uniprot ID:
- P77790
- Molecular weight:
- 21213
Reactions
| D-Ala-D-Ala + H(2)O = 2 D-Ala. |
- General function:
- Involved in transporter activity
- Specific function:
- Part of the ABC transporter complex ddpABCDF, which is probably involved in D,D-dipeptide transport
- Gene Name:
- ddpA
- Uniprot ID:
- P76128
- Molecular weight:
- 57641
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
- General function:
- Involved in transporter activity
- Specific function:
- Part of the ABC transporter complex ddpABCDF, which is probably involved in D,D-dipeptide transport. Probably responsible for the translocation of the substrate across the membrane
- Gene Name:
- ddpB
- Uniprot ID:
- P77308
- Molecular weight:
- 37345
- General function:
- Involved in transporter activity
- Specific function:
- Part of the ABC transporter complex ddpABCDF, which is probably involved in D,D-dipeptide transport. Probably responsible for the translocation of the substrate across the membrane
- Gene Name:
- ddpC
- Uniprot ID:
- P77463
- Molecular weight:
- 31971
- General function:
- Involved in nucleotide binding
- Specific function:
- Part of the ABC transporter complex ddpABCDF, which is probably involved in D,D-dipeptide transport. Probably responsible for energy coupling to the transport system
- Gene Name:
- ddpD
- Uniprot ID:
- P77268
- Molecular weight:
- 36100
- General function:
- Involved in nucleotide binding
- Specific function:
- Part of the binding-protein-dependent transport system for dipeptides. Probably responsible for energy coupling to the transport system
- Gene Name:
- dppD
- Uniprot ID:
- P0AAG0
- Molecular weight:
- 35844
- General function:
- Involved in transporter activity
- Specific function:
- Non-specific porin
- Gene Name:
- ompN
- Uniprot ID:
- P77747
- Molecular weight:
- 41220
- General function:
- Involved in nucleotide binding
- Specific function:
- Part of the binding-protein-dependent transport system for dipeptides. Probably responsible for energy coupling to the transport system
- Gene Name:
- dppF
- Uniprot ID:
- P37313
- Molecular weight:
- 37560
- 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:
- Part of the ABC transporter complex ddpABCDF, which is probably involved in D,D-dipeptide transport. Probably responsible for energy coupling to the transport system
- Gene Name:
- ddpF
- Uniprot ID:
- P77622
- Molecular weight:
- 34621
- General function:
- Involved in transporter activity
- Specific function:
- Dipeptide-binding protein of a transport system that can be subject to osmotic shock. DppA is also required for peptide chemotaxis
- Gene Name:
- dppA
- Uniprot ID:
- P23847
- Molecular weight:
- 60293
- 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 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 transporter activity
- Specific function:
- Part of the ABC transporter complex ddpABCDF, which is probably involved in D,D-dipeptide transport
- Gene Name:
- ddpA
- Uniprot ID:
- P76128
- Molecular weight:
- 57641