Record Information |
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Version | 2.0 |
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Creation Date | 2012-05-31 13:51:08 -0600 |
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Update Date | 2015-09-13 12:56:11 -0600 |
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Secondary Accession Numbers | |
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Identification |
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Name: | Diaminopimelic acid |
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Description | Diaminopimelic acid (DAP) is an amino acid, representing an epsilon-carboxy derivative of lysine. DAP found in the cell walls of E. coli and is a component of peptidoglycan of Gram-negative bacteria. |
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Structure | |
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Synonyms: | - ( (R*,S*)-2,6-diamino-Heptanedioate
- ( (R*,S*)-2,6-diamino-Heptanedioic acid
- (2R,6S)-2,6-diamino-heptanedioate
- (2R,6S)-2,6-diamino-heptanedioic acid
- (R*,S*)-2,6-diamino-Heptanedioate
- (R*,S*)-2,6-diamino-Heptanedioic acid
- 2,6-Diamino-Heptanedioate
- 2,6-Diamino-Heptanedioic acid
- 2,6-Diaminoheptanedioate
- 2,6-Diaminoheptanedioic acid
- 2,6-Diaminopimelate
- 2,6-Diaminopimelic acid
- A,a'-Diaminopimelate
- A,a'-Diaminopimelic acid
- A,e-Diaminopimelate
- A,e-Diaminopimelic acid
- D,L-Diaminopimelate
- D,L-Diaminopimelic acid
- D,L-Meso-diaminoheptanedioate
- D,L-Meso-diaminoheptanedioic acid
- DAPA
- Diaminopimelate
- Diaminopimelic acid
- Dl-2,6-Diaminoheptanedioate
- Dl-2,6-Diaminoheptanedioic acid
- DL-2,6-Diaminopimelate
- DL-2,6-Diaminopimelic acid
- DPA
- L,L-2,6-Diaminoheptanedioate
- L,L-2,6-Diaminoheptanedioic acid
- L,L-2,6-Diaminopimelate
- L,L-2,6-Diaminopimelic acid
- L,L-A2pm
- L,L-DAP
- L,L-Diaminopimelate
- L,L-Diaminopimelic acid
- LL-2,6-diaminoheptanedioate
- LL-2,6-diaminoheptanedioic acid
- LL-2,6-Diaminopimelate
- LL-2,6-Diaminopimelic acid
- meso-1-a,epsilon-Diaminopimelate
- meso-1-a,epsilon-Diaminopimelic acid
- Meso-1-alpha,epsilon-diaminopimelate
- Meso-1-alpha,epsilon-diaminopimelic acid
- meso-1-α,epsilon-Diaminopimelate
- meso-1-α,epsilon-Diaminopimelic acid
- Meso-2,6-diamino-Heptanedioate
- Meso-2,6-diamino-Heptanedioic acid
- Meso-2,6-diaminoheptanedioate
- Meso-2,6-diaminoheptanedioic acid
- meso-a,Alpha'-diaminopimelate
- meso-a,Alpha'-diaminopimelic acid
- meso-a,epsilon-Diaminopimelate
- meso-a,epsilon-Diaminopimelic acid
- Meso-alpha,alpha'-Diaminopimelate
- Meso-alpha,alpha'-Diaminopimelic acid
- Meso-alpha,epsilon-Diaminopimelate
- Meso-alpha,epsilon-Diaminopimelic acid
- Meso-diaminoheptanedioate
- Meso-diaminoheptanedioic acid
- Meso-diaminopimelate
- Meso-diaminopimelic acid
- meso-α,Alpha'-diaminopimelate
- meso-α,Alpha'-diaminopimelic acid
- meso-α,epsilon-Diaminopimelate
- meso-α,epsilon-Diaminopimelic acid
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Chemical Formula: | C7H14N2O4 |
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Weight: | Average: 190.1971 Monoisotopic: 190.095356946 |
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InChI Key: | GMKMEZVLHJARHF-WHFBIAKZSA-N |
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InChI: | InChI=1S/C7H14N2O4/c8-4(6(10)11)2-1-3-5(9)7(12)13/h4-5H,1-3,8-9H2,(H,10,11)(H,12,13)/t4-,5-/m0/s1 |
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CAS number: | 583-93-7 |
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IUPAC Name: | (2S,6S)-2,6-diaminoheptanedioic acid |
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Traditional IUPAC Name: | diamino-pimelic acid |
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SMILES: | N[C@@H](CCC[C@H](N)C(O)=O)C(O)=O |
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Chemical Taxonomy |
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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. |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Carboxylic acids and derivatives |
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Sub Class | Amino acids, peptides, and analogues |
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Direct Parent | L-alpha-amino acids |
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Alternative Parents | |
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Substituents | - L-alpha-amino acid
- Medium-chain fatty acid
- Amino fatty acid
- Dicarboxylic acid or derivatives
- Fatty acid
- Fatty acyl
- Amino acid
- Carboxylic acid
- Organopnictogen compound
- Organic nitrogen compound
- Amine
- Organic oxygen compound
- Primary amine
- Organooxygen compound
- Organonitrogen compound
- Primary aliphatic amine
- Carbonyl group
- Hydrocarbon derivative
- Organic oxide
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Physical Properties |
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State: | Solid |
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Charge: | 0 |
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Melting point: | 300 °C |
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Experimental Properties: | |
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Predicted Properties | |
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Biological Properties |
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Cellular Locations: | Cytoplasm |
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Reactions: | Diaminopimelic acid + Adenosine triphosphate + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamate > ADP + Hydrogen ion + Phosphate + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminoheptanedioateL-alanine-D-glutamate-meso-2,6-diaminoheptanedioate + Water > Diaminopimelic acid + L-Alanyl-D-glutamateWater + N-Succinyl-L,L-2,6-diaminopimelate <> Diaminopimelic acid + Succinic acidDiaminopimelic acid + Hydrogen ion > Carbon dioxide + L-LysineDiaminopimelic acid <> Meso-2,6-DiaminoheptanedioateDiaminopimelic acid <> <i>meso</i>-diaminopimelateN-succinyl-L-2,6-diaminoheptanedioate + Water > Succinic acid + Diaminopimelic acidDiaminopimelic acid > Meso-2,6-DiaminoheptanedioateN-Succinyl-L,L-2,6-diaminopimelate + Water > Succinic acid + Diaminopimelic acidWater + N-Succinyl-L,L-2,6-diaminopimelate <> Diaminopimelic acid + Succinic acid |
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SMPDB Pathways: | |
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KEGG Pathways: | |
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EcoCyc Pathways: | |
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Concentrations |
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| Not Available |
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Spectra |
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Spectra: | Spectrum Type | Description | Splash Key | |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS) | splash10-0umi-1950000000-749403a0eb6d05c7903e | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS) | splash10-0uk9-1980000000-1b092f9141e7549bee24 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0umi-1950000000-749403a0eb6d05c7903e | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0uk9-1980000000-1b092f9141e7549bee24 | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-00dm-9500000000-5d0aafd0747a1090e055 | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive | splash10-014i-4590000000-b941e92697a8b7800912 | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | View in JSpectraViewer |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-004l-0900000000-d85213bd7ac426f10cd7 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-001i-9100000000-add590f1b216bdb40334 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-001i-9000000000-de98ed3bb8c48b6f9852 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - 10V, Positive | splash10-004i-0900000000-2c8a0ca138ef6ea5ef43 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - 20V, Positive | splash10-003r-9600000000-19f54d2417fe44d0eba3 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - 10V, Negative | splash10-000i-0900000000-e8b0bbffeaa501a6fedd | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - 40V, Positive | splash10-0a4i-9000000000-91296097628a67dd97ef | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - 40V, Positive | splash10-0a4i-9000000000-e5c4e034dcab0695e0ce | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - 35V, Negative | splash10-002r-0900000000-2a19445fee9eade1d538 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - 40V, Negative | splash10-00di-9000000000-f44538bc8ae3a51cbbc6 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - 20V, Positive | splash10-003r-9700000000-3baa36a29b4ed6172da0 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - 10V, Positive | splash10-004i-1900000000-cf39d89ce72ac9ddaf51 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - 20V, Negative | splash10-0200-6900000000-6f21b7798408480c1bfc | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - 20V, Positive | splash10-001i-9300000000-6e778092666f89ff4211 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - 10V, Positive | splash10-004i-0900000000-28fbb202ae5558af7594 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - 35V, Positive | splash10-004i-1900000000-8a1ee3da7fbe94f840c2 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - 40V, Positive | splash10-0a4i-9000000000-8caae42eda716644fdc1 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0005-1900000000-be94a16bee7fad24d5d9 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0002-5900000000-896859ce722942f9dd68 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-006t-9200000000-50c1b5a4f7b19e8ff0db | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000i-0900000000-5ecd829b51ba774883f6 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-000i-1900000000-53b7aee01233b5b73d3e | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-00di-9400000000-2cc35eb21a44b2d472b5 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0079-0900000000-a0ce1f9601e9b8d83ccf | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-00dj-6900000000-cc22f522673c5549366c | View in MoNA |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | View in JSpectraViewer |
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References |
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References: | - Borruat G, Roten CA, Fay LB, Karamata D: A high-performance liquid chromatography method for the detection of diaminopimelic acid in urine. Anal Biochem. 2001 Apr 1;291(1):11-6. Pubmed: 11262151
- Hamaker BR, Rivera K, Morales E, Graham GG: Effect of dietary fiber and starch on fecal composition in preschool children consuming maize, amaranth, or cassava flours. J Pediatr Gastroenterol Nutr. 1991 Jul;13(1):59-66. Pubmed: 1656007
- Iida S, Taniguchi H, Kageyama A, Yazawa K, Chibana H, Murata S, Nomura F, Kroppenstedt RM, Mikami Y: Gordonia otitidis sp. nov., isolated from a patient with external otitis. Int J Syst Evol Microbiol. 2005 Sep;55(Pt 5):1871-6. Pubmed: 16166681
- Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
- Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
- Ladesic B, Tomasic J, Kveder S, Hrsak I: The metabolic fate of 14C-labeled immunoadjuvant peptidoglycan monomer. II. In vitro studies. Biochim Biophys Acta. 1981 Nov 18;678(1):12-7. Pubmed: 6118181
- van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
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Synthesis Reference: | Gao, Yong. Synthesis of diaminopimelic acid (DAP) and analogues: mechanistic studies on DAP aminotransferase, epimerase and dehydrogenase. (1998), 166 pp. |
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Material Safety Data Sheet (MSDS) | Download (PDF) |
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Links |
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External Links: | |
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