2,6-diaminopimelic acid

Structural formula
Structure without stereochemistry
General
Surname	2,6-diaminopimelic acid
other names	DAP
Molecular formula	C 7 H 14 N 2 O 4
Brief description	white solid
External identifiers / databases
CAS number 583-93-7 ( mixture of stereoisomers) 922-54-3 ( meso - 2,6 -diaminopimelic acid) 2577-62-0 [(2 R , 6 R ) -2,6-diaminopimelic acid] 14289-34-0 [(2 S , 6 S ) -2,6-diaminopimelic acid] EC number 209-524-6 ECHA InfoCard 100.008.660 PubChem 865 ChemSpider 842 Wikidata Q30126674
properties
Molar mass	190.09 g mol −1
Physical state	firmly
Melting point	295 ° C (decomposition)
safety instructions
GHS labeling of hazardous substances Caution H and P phrases H: 315-319-335 P: 261-305 + 351 + 338
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

2,6-Diaminopimelic acid ( DAP ) is - unless otherwise stated - a mixture of three stereoisomeric organic-chemical compounds that belongs to the group of amino acids .

Structure and stereochemistry

Diaminopimelic acid consists of a C7 chain with terminal carboxy groups . There is an amino group on each of the adjacent carbon atoms . Diaminopimelic acid is similar to lysine , but has an additional carboxy group. The molecule is amphoteric because it contains both acidic and basic groups.

The 2,6-diaminopimelic acid contains two stereocenters which are equally substituted. There are therefore three stereoisomers, the (2 S , 6 S ) form, the mirror image (2 R , 6 R ) form and the meso form.

Biological importance

Diaminopimelic acid is of greatest importance as a component of peptidoglycans , substances that occur in the cell wall of gram-negative and gram-positive bacteria , whereby diaminopimelic acid is only present in peptidoglycans of gram-negative bacteria, while in gram-positive bacteria diaminopimelic acid is substituted with L-lysine. In the meso form , diaminopimelic acid and other amino acids link the carbohydrates of N -acetylmuramic acid , which together with N -acetylglucosamine form the sugar backbone of peptidoglycan. Diaminopimelic acid is not a proteinogenic amino acid .

Individual evidence

1. ↑ Data sheet 2,6-diaminopimelic acid from Acros, accessed on February 20, 2010.
2. ↑ ^{a b c} data sheet 2,6-Diaminopimelic acid from Sigma-Aldrich , accessed on February 12, 2019 ( PDF ).
3. ↑ Michael T. Madigan, John M. Martinko: Brock Microbiology. Pearson Studies, 11th Edition, 2006, ISBN 3-8274-0566-1 .