Diaminopimelic acid

Diaminopimelic acid
Names
Preferred IUPAC name
(2R,6S)-2,6-Diaminoheptanedioic acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.008.660 Edit this at Wikidata
MeSH Diaminopimelic+acid
UNII
  • 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+ checkY
    Key: GMKMEZVLHJARHF-SYDPRGILSA-N checkY
  • O=C(O)[C@@H](N)CCC[C@@H](N)C(=O)O
Properties
C7H14N2O4
Molar mass 190.20 g/mol
Appearance white powder
Density 1.344 g/mL
Melting point 295 °C (563 °F; 568 K)
Boiling point 426.7 °C (800.1 °F; 699.8 K)
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Irritant
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Not to be confused with 2,3-Diaminopropionic acid.

Diaminopimelic acid (DAP) is an amino acid, representing an epsilon-carboxy derivative of lysine. meso-α,ε-Diaminopimelic acid is the last intermediate in the biosynthesis of lysine and undergoes decarboxylation by diaminopimelate decarboxylase to give the final product.[1]

DAP is a characteristic of certain cell walls[2] of some bacteria. DAP is often found in the peptide linkages of NAM-NAG chains that make up the cell wall of gram-negative bacteria. When provided, they exhibit normal growth. When in deficiency, they still grow but with the inability to make new cell wall peptidoglycan.

This is also the attachment point for Braun's lipoprotein.[3]

See also

Images

An alternate view of the DAP structure.

References

  1. ^ Voet, Donald; Voet, Judith G. (2011). Biochemistry (4th ed.). Hoboken, NJ: John Wiley & Sons. pp. 1072–1075. ISBN 978-0-470-57095-1. OCLC 690489261.
  2. ^ Brooks, George H.; Geo F. Brooks (2007). Jawetz, Melnick & Adelberg's medical microbiology. McGraw-Hill Medical. pp. 85. ISBN 978-0-07-147666-9.
  3. ^ Seltmann, Guntram; Holst, Otto (2002). The Bacterial Cell Wall. Berlin: Springer. pp. 81–82. ISBN 3-540-42608-6.


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