Dipicolinic acid

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Dipicolinic acid[1]
Dipicolinic acid.png
Names
Preferred IUPAC name
Pyridine-2,6-dicarboxylic acid
Other names
2,6-Pyridinedicarboxylic acid
Identifiers
3D model (Jmol)
ChEBI
ChemSpider
DrugBank
ECHA InfoCard 100.007.178
Properties
C7H5NO4
Molar mass 167.12 g·mol−1
Melting point 248 to 250 °C (478 to 482 °F; 521 to 523 K)
Hazards
Main hazards Irritant (Xi)
R-phrases R36/37/38
S-phrases S26 S36
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Dipicolinic acid (pyridine-2,6-dicarboxylic acid or PDC and DPA) is a chemical compound which composes 5% to 15% of the dry weight of bacterial spores.[2][3] It is implicated as responsible for the heat resistance of the endospore.[2][4]

However, mutants resistant to heat but lacking dipicolinic acid have been isolated, suggesting other mechanisms contributing to heat resistance are at work.[5]

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.[6]

Two genera of bacterial pathogens are known to produce endospores: the aerobic Bacillus and anaerobic Clostridium.[7]

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] though ironically this phenomenon was first investigated for using DPA in an assay for terbium by Barela and Sherry.[9] Extensive subsequent work by numerous scientists has elaborated on and further developed this approach.

It is also used to prepare dipicolinato ligated lanthanide and transition metal complexes for ion chromatography.[1]

Environmental Behavior[edit]

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]

References[edit]

  1. ^ a b 2,6-Pyridinedicarboxylic acid at Sigma-Aldrich
  2. ^ a b Sliemandagger, TA.; Nicholson, WL. (2001). "Role of Dipicolinic Acid in Survival of Bacillus subtilis Spores Exposed to Artificial and Solar UV Radiation". Applied and Environmental Microbiology. 67 (3): 1274–1279. doi:10.1128/aem.67.3.1274-1279.2001. PMC 92724Freely accessible. PMID 11229921. 
  3. ^ Sci-Tech Dictionary. McGraw-Hill Dictionary of Scientific and Technical Terms, McGraw-Hill Companies, Inc.
  4. ^ Madigan, M., J Martinko, J. Parker (2003). Brock Biology of Microorganisms, 10th edition. Pearson Education, Inc., ISBN 981-247-118-9.
  5. ^ Prescott, L. (1993). Microbiology, Wm. C. Brown Publishers, ISBN 0-697-01372-3.
  6. ^ Madigan. M, Martinko. J, Bender. K, Buckley. D, Stahl. D, (2014), Brock Biology of Microorganisms, 14th Edition, p. 78, Pearson Education Inc., ISBN 978-0-321-89739-8.
  7. ^ Gladwin, M. (2008). Clinical Microbiology Made Ridiculously Simple, MedMaster, Inc., ISBN 0-940780-81-X.
  8. ^ Rosen, D.L.; Sharpless, C.; McGown, L.B. (1997). "Bacterial Spore Detection and Determination by Use of Terbium Dipicolinate Photoluminescence". Analytical Chemistry. 69 (6): 1082–1085. doi:10.1021/ac960939w. 
  9. ^ Barela, T.D.; Sherry, A.D. (1976). "A simple, one step fluorometric method for determination of nanomolar concentrations of terbium". Analytical Biochemistry. 71 (2): 351–357. doi:10.1016/s0003-2697(76)80004-8. 
  10. ^ Sims, G. K.; O'Loughlin, E.J. (1989). "Degradation of pyridines in the environment". CRC Critical Reviews in Environmental Control. 19 (4): 309–340. doi:10.1080/10643388909388372. 
  11. ^ Sims, G. K.; Sommers, L.E. (1986). "Biodegradation of pyridine derivatives in soil suspensions". Environmental Toxicology and Chemistry. 5 (6): 503–509. doi:10.1002/etc.5620050601. 
  12. ^ Ratledge, Colin (ed). 2012. Biochemistry of microbial degradation. Springer Science and Business Media Dordrecht, Netherlands. 590 pages . doi:10.1007/978-94-011-1687-9
  13. ^ Annonymous. MSDS. pyridine-2-6-carboxylic-acid .Jubilant Organosys Limited. http://www.jubl.com/uploads/files/39msds_msds-pyridine-2-6-carboxylic-acid.pdf

External links[edit]