Diaminopimelic acid

Names
IUPAC name (2R,6S)-2,6-Diaminoheptanedioic acid
Identifiers
CAS Registry Number	583-93-7 N
ChEBI	CHEBI:16488 Y
ChEMBL	ChEMBL415306 Y
ChemSpider	89700 Y
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
Jmol-3D images	Image
MeSH	Diaminopimelic+acid
PubChem	1549101
SMILES O=C(O)[C@@H](N)CCC[C@@H](N)C(=O)O
Properties
Molecular formula	C7H14N2O4
Molar mass	190.20 g·mol−1
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 noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
N verify (what is: Y/N?)
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[edit]

• Peptidoglycan
• Pimelic acid
• cell wall

Images[edit]

An alternate view of the DAP structure.

References[edit]