Diaminopimelic acid

Diaminopimelic acid
Names


IUPAC name (2R,6S)-2,6-Diaminoheptanedioic acid
Identifiers
CAS Number	583-93-7^N
3D model (Jmol)	Interactive image
ChEBI	CHEBI:16488^Y
ChEMBL	ChEMBL415306^Y
ChemSpider	89700^Y
ECHA InfoCard	100.008.660
IUPHAR/BPS	5021
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)
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

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]

Images

An alternate view of the DAP structure.

References

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

Microbiology: Bacteria

Medical
microbiology

Biochemistry
and ecology

Oxygen preference	Aerobic Obligate Anaerobic Facultative Obligate Microaerophile Nanaerobe Aerotolerant

Other	Microbial metabolism Primary nutritional groups Nitrogen fixation Microbial ecology Human flora Gut flora Skin flora Vaginal flora Substrate preference Lipophilic Saccharophilic

Morphology:
Shapes

Morphology:
Structures

Cell envelope	Cell membrane Cell wall: Peptidoglycan NAM NAG DAP Gram-positive bacteria only: Teichoic acid Lipoteichoic acid Endospore Gram-negative bacteria only: Bacterial outer membrane Porin Lipopolysaccharide Periplasmic space Mycobacteria only: Arabinogalactan Mycolic acid

Outside envelope	Bacterial capsule Slime layer S-layer Glycocalyx Pilus Fimbria

Composite	Biofilm

Bacterial
taxonomy

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Diaminopimelic acid

See also

Images

References