Chemistry:Diaminopimelic acid

Diaminopimelic acid

Names
Preferred IUPAC name (2R,6S)-2,6-Diaminoheptanedioic acid
Identifiers
CAS Number	583-93-7 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:16488 Y
ChEMBL	ChEMBL415306 Y
ChemSpider	89700 Y
IUPHAR/BPS	5021
MeSH	Diaminopimelic+acid
PubChem CID	1549101
UNII	V5KRL7N7GD 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
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).
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Infobox references

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

DAP is a characteristic of certain cell walls 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.

See also

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

Images

An alternate view of the DAP structure.