2,6-DIAMINOPIMELIC ACID

PRODUCT IDENTIFICATION

CAS RN

583-93-7

EINECS RN

209-524-6

FORMULA

MOLE WEIGHT

H.S CODE

SMILES

CLASSIFICATION

Diamino Acid, Dipeptide

EXTRA NOTES

PHYSICAL AND CHEMICAL PROPERTIES

PHYSICAL STATE.

MELTING POINT

295 C

BOILING POINT

DENSITY

SOLUBILITY IN WATER

0.90%

VAPOR DENSITY

log P(octanol-water)

VAPOR PRESSURE

AUTOIGNITION TEMP

REFRACTIVE INDEX

FLASH POINT

INCOMPATIBLE MATERIALS

Strong oxidizing agents

Has not been reported

NFPA RATINGS

Health: 1; Flammability: 0; Instability: 0;

EXTERNAL LINKS & GENERAL DESCRIPTION

Wikipedia Linking - Diaminopimelic acid

Google Scholar Search - 2,6-Diaminopimelic acid

PubChem Compound Summary - 2,6-Diaminopimelic acid

KEGG (Kyoto Encyclopedia of Genes and Genomes) -  Diaminopimelic acid

http://www.ebi.ac.uk/ -  Diaminopimelic acid

http://www.ncbi.nlm.nih.gov/ - Diaminopimelic acid

http://toxnet.nlm.nih.gov/
Biosynthesis of lysine and meso-diaminopimelic acid in bacteria provides essential components for protein synthesis and construction of the bacterial peptidoglycan cell wall. The dapE operon enzymes synthesize both meso-diaminopimelic acid and lysine and, therefore, represent potential targets for novel antibacterials. The dapE-encoded N-succinyl-L,L-diaminopimelic acid desuccinylase functions in a late step of the pathway and converts N-succinyl-L,L-diaminopimelic acid to L,L-diaminopimelic acid and succinate. Deletion of the dapE gene is lethal to Helicobacter pylori and Mycobacterium smegmatis, indicating that DapE's are essential for cell growth and proliferation. Since there are no similar pathways in humans, inhibitors that target DapE may have selective toxicity against only bacteria. A major limitation in developing antimicrobial agents that target DapE has been the lack of structural information. Herein, we report the high-resolution X-ray crystal structures of the DapE from Haemophilus influenzae with one and two zinc ions bound in the active site, respectively. These two forms show different activity. Based on these newly determined structures, we propose a revised catalytic mechanism of peptide bond cleavage by DapE enzymes. These structures provide important insight into catalytic mechanism of DapE enzymes as well as a structural foundation that is critical for the rational design of DapE inhibitors.

http://mic.sgmjournals.org/
The role of diaminopimelic acid (DAP) as a key intermediate in the biosynthesis of lysine in bacteria is now well established (see review by Work, 1960). It has also been shown to be present in the mucopeptide component of a number of Gram-positive bacteria and in all the Gram-negative bacteria so far examined (Salton, 1964). Whereas the other dibasic amino acids found in the mucopeptide of Gram-positive bacteria have been shown to exist in the L-configuration, DAP has been found as both LL- and meso-isomers (Hoare & Work, 1957), although the latter is the most widely distributed. In Gram-negative bacteria, where the mucopeptide makes up a much smaller proportion of the wall, the DAP-isomer present has been thoroughly investigated in only a few species, The meso-isomer has been identified chromatographically in all the Gram-negative bacteria studied and firmly identified in Aerobacter cloacae (Anwar, Roy & Watson, 1963) and in Escherichia coli (Diringer & Jusic, 1966). There have been no reports of the occurrence of either the LL- or DD-isomers in walls of Gram-negative bacteria. An opportunity to study the role of DAP in pseudomonads arose from the isolation of lysine auxotrophs, one of which was shown to be deficient in diaminopimelate epimerase (EC 5 . I . I .7). This paper reports their growth requirements, wall composition and response to antibiotics known to interfere with wall synthesis.

SALES SPECIFICATION

APPEARANCE

white to tan powder

ASSAY

98.0% min (Sum of isomers)

TRANSPORT & REGULATORY INFORMATION

UN NO.

Not regulated

HAZARD SYMBOL

SAFETY INFORMATION

HAZARD OVERVIEW

OSHA Hazards: Irritant. May cause eye and skin irritation. May cause respiratory and digestive tract irritation. Target Organs: No data found.

GHS

SIGNAL WORD

Warning

PICTOGRAMS

HAZARD STATEMENTS

H315-H319-H335

P STATEMENTS

P261-P305 + P351 + P338

RISK PHRASES

SAFETY PHRASES

PACKING

PRICE INFORMATION