Diaminopimelic acid

DAP

• 583-93-7 ( mixture of stereoisomers )
• 922-54-3 ( meso -2 ,6- diaminopimelic acid )
• 2577-62-0 [( 2R, 6R ) -2,6- diaminopimelic ]
• 14289-34-0 [( 2S, 6S ) -2,6- diaminopimelic ]

White solid

Fixed

300 ° C ( decomposition)

Attention

Template: Infobox chemical / molecular formula search available

2,6- diaminopimelic acid (DAP ) is an organic compound belonging to the group of amino acids.

Construction

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

Biological Significance

The greatest importance is diaminopimelic acid as a component of peptidoglycan, substances that occur in the cell wall of gram-negative and gram-positive bacteria. In the meso- form of diaminopimelic acid linked together with other amino acids of the N - acetylmuramic acid carbohydrate with each other, which together with the N- acetylglucosamine of peptidoglycan backbone of the sugar. Diaminopimelic acid is not a proteinogenic amino acid.

Stereochemistry

2,6- diaminopimelic acid contains two stereogenic centers, which are identically substituted. There are thus three stereoisomers, the (2S, 5S )-form, the mirror image to the (2R, 5R )-form and the meso form.