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
ECHA InfoCard	100.008.660
IUPHAR/BPS	5021
MeSH	Diaminopimelic+acid
PubChem CID	1549101
UNII	V5KRL7N7GD^Y
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
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
Occupational safety and health (OHS/OSH):
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

Chemical compound

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 peptidoglycan.

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

Images

References

^ Brooks, George H.; Geo F. Brooks (2007). Jawetz, Melnick & Adelberg's medical microbiology. McGraw-Hill Medical. pp. 85. ISBN 978-0-07-147666-9.
^ 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 Facultative Anaerobic Facultative Obligate Microaerophile Nanaerobe Aerotolerant
Other	Extremophile Human microbiome Gut Lung Mouth Skin Vaginal (in pregnancy) Placental Uterine Salivary Microbial metabolism Nitrogen fixation Microbial ecology Primary nutritional groups Substrate preference Lipophilic Saccharophilic

Shape

Bacterial cellular morphologies
- cell structure
- plasticity
Cocci
Bacilli
Coccobacilli
Spiral

Structure

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 Non-motile bacteria
Composite	Biofilm