Diaminopimelic acid

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

Diaminopimelic acid

Names
IUPAC name (2R,6S)-2,6-Diaminoheptanedioic acid
Identifiers
CAS Number	583-93-7^N
3D model (JSmol)	Interactive image
ChEBI	CHEBI:16488^Y
ChEMBL	ChEMBL415306^Y
ChemSpider	89700^Y
ECHA InfoCard	100.008.660
IUPHAR/BPS	5021
MeSH	Diaminopimelic+acid
PubChem CID	1549101
CompTox Dashboard (EPA)	DTXSID10862237
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+^Y Key: GMKMEZVLHJARHF-SYDPRGILSA-N^Y InChI=1/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+ Key: GMKMEZVLHJARHF-SYDPRGILBU
SMILES O=C(O)[C@@H](N)CCC[C@@H](N)C(=O)O
Properties
Chemical formula	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 ^YN ?)
Infobox references

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 peptidoglycan.

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

See also

• Peptidoglycan
• Pimelic acid
• Aspartate-semialdehyde dehydrogenase, an enzyme involved in DAP synthesis

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. pp. 85. ISBN 978-0-07-147666-9.
2. Seltmann, Guntram; Holst, Otto (2002). The Bacterial Cell Wall. Berlin: Springer. pp. 81–82. ISBN 3-540-42608-6.