Diaminopimelic acid

Diaminopimelic acid
Names
IUPAC name
(2R,6S)-2,6-Diaminoheptanedioic acid
Identifiers
583-93-7 N
ChEBI CHEBI:16488 YesY
ChEMBL ChEMBL415306 YesY
ChemSpider 89700 YesY
5021
Jmol interactive 3D Image
MeSH Diaminopimelic+acid
PubChem 1549101
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
Main hazards Irritant
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

Diaminopimelic acid (DAP) is an amino acid, representing an epsilon-carboxy derivative of lysine.

DAP is a characteristic of certain cell walls[1] 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 proteoglycan.

This is also the attachment point for Braun's lipoprotein.[2]

See also

Images

An alternate view of the DAP structure.

References

  1. ↑ Brooks, George H.; Geo F. Brooks (2007). Jawetz, Melnick & Adelberg's medical microbiology. McGraw-Hill Medical. p. 85. ISBN 0-07-147666-0.
  2. ↑ Seltmann, Guntram; Holst, Otto (2002). The Bacterial Cell Wall. Berlin: Springer. pp. 81–82. ISBN 3-540-42608-6.
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