Record Information |
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Version | 1.0 |
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Created at | 2020-11-23 19:38:55 UTC |
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Updated at | 2021-08-12 19:51:58 UTC |
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NP-MRD ID | NP0002726 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | DL-alpha,epsilon-Diaminopimelic acid |
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Provided By | BMRB |
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Description | Meso-diaminopimelate 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. It was first documented in 2001 (PMID: 11262151). Based on a literature review a significant number of articles have been published on meso-diaminopimelate (PMID: 17984079) (PMID: 20803494) (PMID: 22339732) (PMID: 23325104). |
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Structure | [H][C@](N)(CCC[C@@]([H])(N)C(O)=O)C(O)=O 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+ |
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Synonyms | Value | Source |
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Meso-diaminoheptanedioic acid | ChEBI | Meso-2,6-diaminopimelate | Kegg | Meso-2,6-diaminopimelic acid | Kegg | Meso-diaminoheptanedioate | Kegg | Meso-diaminopimelic acid | Generator | meso-2,6-Diaminoheptanedioic acid | Generator |
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Chemical Formula | C7H14N2O4 |
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Average Mass | 190.1971 Da |
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Monoisotopic Mass | 190.09536 Da |
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IUPAC Name | (2R,6S)-2,6-diaminoheptanedioic acid |
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Traditional Name | diaminopimelic acid |
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CAS Registry Number | Not Available |
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SMILES | [H][C@](N)(CCC[C@@]([H])(N)C(O)=O)C(O)=O |
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InChI Identifier | 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+ |
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InChI Key | GMKMEZVLHJARHF-SYDPRGILSA-N |
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Experimental Spectra |
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| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Predicted Spectra |
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| Not Available | Chemical Shift Submissions |
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| Not Available | Species |
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Species of Origin | Not Available |
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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 | - D-alpha-amino acid
- 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
- Organic oxide
- Hydrocarbon derivative
- 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 | Not Available |
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Experimental Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | |
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General 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 ]
- Ulrich EL, Akutsu H, Doreleijers JF, Harano Y, Ioannidis YE, Lin J, Livny M, Mading S, Maziuk D, Miller Z, Nakatani E, Schulte CF, Tolmie DE, Kent Wenger R, Yao H, Markley JL: BioMagResBank. Nucleic Acids Res. 2008 Jan;36(Database issue):D402-8. doi: 10.1093/nar/gkm957. Epub 2007 Nov 4. [PubMed:17984079 ]
- Toth GK, Hetenyi A, Ilisz I, Peter A: A simple chromatographic route for the isolation of meso diaminopimelic acid. Chirality. 2011 Feb;23(2):133-7. doi: 10.1002/chir.20888. Epub 2010 Aug 27. [PubMed:20803494 ]
- Usha V, Lloyd AJ, Lovering AL, Besra GS: Structure and function of Mycobacterium tuberculosis meso-diaminopimelic acid (DAP) biosynthetic enzymes. FEMS Microbiol Lett. 2012 May;330(1):10-6. doi: 10.1111/j.1574-6968.2012.02527.x. Epub 2012 Mar 7. [PubMed:22339732 ]
- Saito Y, Yoshimura Y, Wakamatsu H, Takahata H: A facile synthesis of fully protected meso-diaminopimelic acid (DAP) and its application to the preparation of lipophilic N-acyl iE-DAP. Molecules. 2013 Jan 16;18(1):1162-73. doi: 10.3390/molecules18011162. [PubMed:23325104 ]
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