2,6-diaminopimelic acid
Structural formula | |||||||||||||||||||
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Structure without stereochemistry | |||||||||||||||||||
General | |||||||||||||||||||
Surname | 2,6-diaminopimelic acid | ||||||||||||||||||
other names |
DAP |
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Molecular formula | C 7 H 14 N 2 O 4 | ||||||||||||||||||
Brief description |
white solid |
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External identifiers / databases | |||||||||||||||||||
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properties | |||||||||||||||||||
Molar mass | 190.09 g mol −1 | ||||||||||||||||||
Physical state |
firmly |
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Melting point |
295 ° C (decomposition) |
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safety instructions | |||||||||||||||||||
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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
- ↑ Data sheet 2,6-diaminopimelic acid from Acros, accessed on February 20, 2010.
- ↑ a b c data sheet 2,6-Diaminopimelic acid from Sigma-Aldrich , accessed on February 12, 2019 ( PDF ).
- ↑ Michael T. Madigan, John M. Martinko: Brock Microbiology. Pearson Studies, 11th Edition, 2006, ISBN 3-8274-0566-1 .