Diaminopimelic acid

Diaminopimelic acid
Names
	Preferred IUPAC name (2R,6S)-2,6-Diaminoheptanedioic acid
Identifiers
CAS Number	583-93-7 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:16488 ;
ChEMBL	ChEMBL415306 ;
ChemSpider	89700 ;
ECHA InfoCard	100.008.660
IUPHAR/BPS	5021;
MeSH	Diaminopimelic+acid
PubChem CID	1549101;
UNII	V5KRL7N7GD ;
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+ Key: GMKMEZVLHJARHF-SYDPRGILSA-N ;
	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). verify (what is ?) Infobox references

Diaminopimelic acid (DAP) is an amino acid, representing an epsilon-carboxy derivative of lysine. meso-α,ε-Diaminopimelic acid is the last intermediate in the biosynthesis of lysine and undergoes decarboxylation by diaminopimelate decarboxylase to give the final product.^[1]

DAP is a characteristic of certain cell walls^[2] 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.^[3]

Images

References

^ Voet, Donald; Voet, Judith G. (2011). Biochemistry (4th ed.). Hoboken, NJ: John Wiley & Sons. pp. 1072–1075. ISBN 978-0-470-57095-1. OCLC 690489261.
^ 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.

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[1] Voet, Donald; Voet, Judith G. (2011). Biochemistry (4th ed.). Hoboken, NJ: John Wiley & Sons. pp. 1072–1075. ISBN 978-0-470-57095-1. OCLC 690489261.

[isbn0-07-147666-0-2] Brooks, George H.; Geo F. Brooks (2007). Jawetz, Melnick & Adelberg's medical microbiology. McGraw-Hill Medical. pp. 85. ISBN 978-0-07-147666-9.

[3] Seltmann, Guntram; Holst, Otto (2002). The Bacterial Cell Wall. Berlin: Springer. pp. 81–82. ISBN 3-540-42608-6.

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Diaminopimelic acid

See also

Images

References