Record Information
Version2.0
Creation Date2012-05-31 13:51:08 -0600
Update Date2015-09-13 12:56:11 -0600
Secondary Accession Numbers
  • ECMDB01370
Identification
Name:Diaminopimelic acid
DescriptionDiaminopimelic 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.
Structure
Thumb
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
Chemical Formula:C7H14N2O4
Weight:Average: 190.1971
Monoisotopic: 190.095356946
InChI Key:GMKMEZVLHJARHF-WHFBIAKZSA-N
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
CAS number:583-93-7
IUPAC Name:(2S,6S)-2,6-diaminoheptanedioic acid
Traditional IUPAC Name:diamino-pimelic acid
SMILES:N[C@@H](CCC[C@H](N)C(O)=O)C(O)=O
Chemical Taxonomy
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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentL-alpha-amino acids
Alternative Parents
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
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:0
Melting point:300 °C
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility14.1 g/LALOGPS
logP-4.1ALOGPS
logP-5.5ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)1.85ChemAxon
pKa (Strongest Basic)9.83ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area126.64 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity43.64 m³·mol⁻¹ChemAxon
Polarizability18.93 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
Lysine biosynthesisPW000771 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)splash10-0umi-1950000000-749403a0eb6d05c7903eView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)splash10-0uk9-1980000000-1b092f9141e7549bee24View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0umi-1950000000-749403a0eb6d05c7903eView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0uk9-1980000000-1b092f9141e7549bee24View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dm-9500000000-5d0aafd0747a1090e055View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-014i-4590000000-b941e92697a8b7800912View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-004l-0900000000-d85213bd7ac426f10cd7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-001i-9100000000-add590f1b216bdb40334View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-001i-9000000000-de98ed3bb8c48b6f9852View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-2c8a0ca138ef6ea5ef43View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-003r-9600000000-19f54d2417fe44d0eba3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-e8b0bbffeaa501a6feddView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-91296097628a67dd97efView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-e5c4e034dcab0695e0ceView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-002r-0900000000-2a19445fee9eade1d538View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-00di-9000000000-f44538bc8ae3a51cbbc6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-003r-9700000000-3baa36a29b4ed6172da0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-004i-1900000000-cf39d89ce72ac9ddaf51View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0200-6900000000-6f21b7798408480c1bfcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-001i-9300000000-6e778092666f89ff4211View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-28fbb202ae5558af7594View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-004i-1900000000-8a1ee3da7fbe94f840c2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-8caae42eda716644fdc1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0005-1900000000-be94a16bee7fad24d5d9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-5900000000-896859ce722942f9dd68View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006t-9200000000-50c1b5a4f7b19e8ff0dbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-5ecd829b51ba774883f6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-1900000000-53b7aee01233b5b73d3eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9400000000-2cc35eb21a44b2d472b5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0079-0900000000-a0ce1f9601e9b8d83ccfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00dj-6900000000-cc22f522673c5549366cView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
References
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
Synthesis Reference:Gao, Yong. Synthesis of diaminopimelic acid (DAP) and analogues: mechanistic studies on DAP aminotransferase, epimerase and dehydrogenase. (1998), 166 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
External Links:
ResourceLink
CHEBI ID23673
HMDB IDHMDB01370
Pubchem Compound ID865
Kegg IDC00666
ChemSpider ID388416
Wikipedia IDDiaminopimelic acid
BioCyc IDLL-DIAMINOPIMELATE
EcoCyc IDLL-DIAMINOPIMELATE

Enzymes

General function:
Involved in catalytic activity
Specific function:
Meso-2,6-diaminoheptanedioate = L-lysine + CO(2)
Gene Name:
lysA
Uniprot ID:
P00861
Molecular weight:
46177
Reactions
Meso-2,6-diaminoheptanedioate = L-lysine + CO(2).
General function:
Involved in diaminopimelate epimerase activity
Specific function:
LL-2,6-diaminoheptanedioate = meso- diaminoheptanedioate
Gene Name:
dapF
Uniprot ID:
P0A6K1
Molecular weight:
30208
Reactions
LL-2,6-diaminoheptanedioate = meso-diaminoheptanedioate.
General function:
Involved in metallopeptidase activity
Specific function:
Catalyzes the hydrolysis of N-succinyl-L,L- diaminopimelic acid (SDAP), forming succinate and LL-2,6- diaminoheptanedioate (DAP), an intermediate involved in the bacterial biosynthesis of lysine and meso-diaminopimelic acid, an essential component of bacterial cell walls
Gene Name:
dapE
Uniprot ID:
P0AED7
Molecular weight:
41269
Reactions
N-succinyl-LL-2,6-diaminoheptanedioate + H(2)O = succinate + LL-2,6-diaminoheptanedioate.
General function:
Involved in ATP binding
Specific function:
Catalyzes the addition of meso-diaminopimelic acid to the nucleotide precursor UDP-N-acetylmuramoyl-L-alanyl-D-glutamate (UMAG) in the biosynthesis of bacterial cell-wall peptidoglycan. Is also able to use many meso-diaminopimelate analogs as substrates, although much less efficiently, but not L-lysine
Gene Name:
murE
Uniprot ID:
P22188
Molecular weight:
53343
Reactions
ATP + UDP-N-acetylmuramoyl-L-alanyl-D-glutamate + meso-2,6-diaminoheptanedioate = ADP + phosphate + UDP-N-acetylmuramoyl-L-alanyl-D-gamma-glutamyl-meso-2,6-diamino-heptanedioate.
General function:
Involved in metallocarboxypeptidase activity
Specific function:
Specific function unknown
Gene Name:
mpaA
Uniprot ID:
P0ACV6
Molecular weight:
26558

Transporters

General function:
Involved in diaminopimelate epimerase activity
Specific function:
LL-2,6-diaminoheptanedioate = meso- diaminoheptanedioate
Gene Name:
dapF
Uniprot ID:
P0A6K1
Molecular weight:
30208
Reactions
LL-2,6-diaminoheptanedioate = meso-diaminoheptanedioate.
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:
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 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