Dipicolinic acid
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Dipicolinic acid (pyridine-2,6-dicarboxylic acid or PDC and DPA) is a chemical compound which plays a role in the heat resistance of bacterial endospores. It is also used to prepare Template:Chem name and transition metal complexes for ion chromatography.[1]
Biological role
Dipicolinic acid composes 5% to 15% of the dry weight of Bacillus subtilis spores.[2][3] It has been implicated as responsible for the heat resistance of the endospore,[2][4] although mutants resistant to heat but lacking dipicolinic acid have been isolated, suggesting other mechanisms contributing to heat resistance are at work.[5] Two genera of bacterial pathogens are known to produce endospores: the aerobic Bacillus and anaerobic Clostridium.[6]
Dipicolinic acid forms a complex with calcium ions within the endospore core. This complex binds free water molecules, causing dehydration of the spore. As a result, the heat resistance of macromolecules within the core increases. The calcium-dipicolinic acid complex also functions to protect DNA from heat denaturation by inserting itself between the nucleobases, thereby increasing the stability of DNA.[7]
Detection
The high concentration of DPA in and specificity to bacterial endospores has long made it a prime target in analytical methods for the detection and measurement of bacterial endospores. A particularly important development in this area was the demonstration by Rosen et al. of an assay for DPA based on photoluminescence in the presence of terbium,[8] although this phenomenon was first investigated for using DPA in an assay for terbium by Barela and Sherry.[9]
Environmental behavior
Simple substituted pyridines vary significantly in environmental fate characteristics, such as volatility, adsorption, and biodegradation.[10] Dipicolinic acid is among the least volatile, least adsorbed by soil, and most rapidly degraded of the simple pyridines.[11] A number of studies have confirmed dipicolinic acid is biodegradable in aerobic and anaerobic environments, which is consistent with the widespread occurrence of the compound in nature.[12] With a high solubility (5g/liter) and limited sorption (estimated Koc = 1.86), utilization of dipicolinic acid as a growth substrate by microorganisms is not limited by bioavailability in nature.[13]
See also
- Dinicotinic acid, an isomeric dicarboxylic acid
- 2,6-Pyridinedicarbothioic acid has both -COOH (carboxylic acid) groups replaced by -COSH (thiocarboxylic acid) groups
References
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- ↑ a b 2,6-Pyridinedicarboxylic acid at Sigma-Aldrich
- ↑ a b Script error: No such module "Citation/CS1".
- ↑ Sci-Tech Dictionary. McGraw-Hill Dictionary of Scientific and Technical Terms, McGraw-Hill Companies, Inc.
- ↑ Madigan, M., J Martinko, J. Parker (2003). Brock Biology of Microorganisms, 10th edition. Pearson Education, Inc., Template:ISBN.
- ↑ Prescott, L. (1993). Microbiology, Wm. C. Brown Publishers, Template:ISBN.
- ↑ Gladwin, M. (2008). Clinical Microbiology Made Ridiculously Simple, MedMaster, Inc., Template:ISBN.
- ↑ Madigan. M, Martinko. J, Bender. K, Buckley. D, Stahl. D, (2014), Brock Biology of Microorganisms, 14th Edition, p. 78, Pearson Education Inc., Template:ISBN.
- ↑ Script error: No such module "Citation/CS1".
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- ↑ Ratledge, Colin (ed). 2012. Biochemistry of microbial degradation. Springer Science and Business Media Dordrecht, Netherlands. 590 pages . Script error: No such module "CS1 identifiers".
- ↑ Anonymous. MSDS. pyridine-2-6-carboxylic-acid .Jubilant Organosys Limited. http://www.jubl.com/uploads/files/39msds_msds-pyridine-2-6-carboxylic-acid.pdf
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External links
- Script error: No such module "Unsubst".JPL Develops High-Speed Test to Improve Pathogen Decontamination Script error: No such module "webarchive". at JPL.
- Script error: No such module "Unsubst". Spotting Spores at Astrobiology Magazine.