Diaminopimelic acid

Diaminopimelic acid

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Names
IUPAC name (2R,6S)-2,6-Diaminoheptanedioic acid
Identifiers
CAS Number	583-93-7 N
ChEBI	CHEBI:16488 Y
ChEMBL	ChEMBL415306 Y
ChemSpider	89700 Y
IUPHAR/BPS	5021
Jmol 3D model	Interactive image
MeSH	Diaminopimelic+acid
PubChem	1549101
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)
Vapor pressure	{{{value}}}
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

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 proteoglycan.

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

See also

• Peptidoglycan
• Pimelic acid
• cell wall

Images

File:DAP-H.png

An alternate view of the DAP structure.