Dipicolinic acid: Difference between revisions

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'''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 [[bacteria]]l spores.<ref name="pyridine">{{cite journal | last1 = Sliemandagger | first1 = TA. | last2 = Nicholson | first2 = WL. | year = 2001 | title = Role of Dipicolinic Acid in Survival of Bacillus subtilis Spores Exposed to Artificial and Solar UV Radiation | url = | journal = Applied and Environmental Microbiology | volume = 67 | issue = 3| pages = 1274–1279 | doi=10.1128/aem.67.3.1274-1279.2001}}</ref><ref>Sci-Tech Dictionary. ''McGraw-Hill Dictionary of Scientific and Technical Terms'', McGraw-Hill Companies, Inc.</ref> It is implicated as responsible for the heat resistance of the [[endospore]].<ref name="pyridine"/><ref>Madigan, M., J Martinko, J. Parker (2003). ''Brock Biology of Microorganisms'', 10th edition. Pearson Education, Inc., ISBN 981-247-118-9.</ref>
'''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 [[bacteria]]l spores.<ref name="pyridine">{{cite journal | last1 = Sliemandagger | first1 = TA. | last2 = Nicholson | first2 = WL. | year = 2001 | title = Role of Dipicolinic Acid in Survival of Bacillus subtilis Spores Exposed to Artificial and Solar UV Radiation | journal = Applied and Environmental Microbiology | volume = 67 | issue = 3| pages = 1274–1279 | doi=10.1128/aem.67.3.1274-1279.2001 | pmid=11229921 | pmc=92724}}</ref><ref>Sci-Tech Dictionary. ''McGraw-Hill Dictionary of Scientific and Technical Terms'', McGraw-Hill Companies, Inc.</ref> It is implicated as responsible for the heat resistance of the [[endospore]].<ref name="pyridine"/><ref>Madigan, M., J Martinko, J. Parker (2003). ''Brock Biology of Microorganisms'', 10th edition. Pearson Education, Inc., ISBN 981-247-118-9.</ref>


However, mutants resistant to heat but lacking dipicolinic acid have been isolated, suggesting other mechanisms contributing to heat resistance are at work.<ref>Prescott, L. (1993). ''Microbiology'', Wm. C. Brown Publishers, ISBN 0-697-01372-3.</ref>
However, mutants resistant to heat but lacking dipicolinic acid have been isolated, suggesting other mechanisms contributing to heat resistance are at work.<ref>Prescott, L. (1993). ''Microbiology'', Wm. C. Brown Publishers, ISBN 0-697-01372-3.</ref>
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==Environmental Behavior==
==Environmental Behavior==
Simple substituted [[pyridines]] vary significantly in environmental fate characteristics, such as [[volatility (chemistry)|volatility]], [[adsorption]], and [[biodegradation]].<ref>Sims, G. K. and E.J. O'Loughlin. 1989. Degradation of pyridines in the environment. CRC Critical Reviews in Environmental Control. 19(4): 309-340. DOI: 10.1080/10643388909388372</ref> Dipicolinic acid is among the least volatile, least adsorbed by soil, and most rapidly degraded of the simple pyridines.<ref>Sims, G. K. and L.E. Sommers. 1986. Biodegradation of pyridine derivatives in soil suspensions. Environmental Toxicology and Chemistry. 5:503-509. DOI: 10.1002/etc.5620050601</ref> A number of studies have confirmed dipicolinic acid is biodegradable in [[aerobic organism|aerobic]] and [[Hypoxia (environmental)|anaerobic]] environments, which is consistent with the widespread occurrence of the compound in nature.<ref>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</ref> 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.<ref>Annonymous. MSDS. pyridine-2-6-carboxylic-acid .Jubilant Organosys Limited. http://www.jubl.com/uploads/files/39msds_msds-pyridine-2-6-carboxylic-acid.pdf</ref>
Simple substituted [[pyridines]] vary significantly in environmental fate characteristics, such as [[volatility (chemistry)|volatility]], [[adsorption]], and [[biodegradation]].<ref>{{cite journal | last1 = Sims | first1 = G. K. | last2 = O'Loughlin | first2 = E.J. | year = 1989 | title = Degradation of pyridines in the environment | url = | journal = CRC Critical Reviews in Environmental Control | volume = 19 | issue = 4| pages = 309–340 | doi = 10.1080/10643388909388372 }}</ref> Dipicolinic acid is among the least volatile, least adsorbed by soil, and most rapidly degraded of the simple pyridines.<ref>{{cite journal | last1 = Sims | first1 = G. K. | last2 = Sommers | first2 = L.E. | year = 1986 | title = Biodegradation of pyridine derivatives in soil suspensions | url = | journal = Environmental Toxicology and Chemistry | volume = 5 | issue = 6| pages = 503–509 | doi = 10.1002/etc.5620050601 }}</ref> A number of studies have confirmed dipicolinic acid is biodegradable in [[aerobic organism|aerobic]] and [[Hypoxia (environmental)|anaerobic]] environments, which is consistent with the widespread occurrence of the compound in nature.<ref>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}}</ref> 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.<ref>Annonymous. MSDS. pyridine-2-6-carboxylic-acid .Jubilant Organosys Limited. http://www.jubl.com/uploads/files/39msds_msds-pyridine-2-6-carboxylic-acid.pdf</ref>


==References==
==References==

Revision as of 09:23, 12 March 2017

Dipicolinic acid[1]
Names
Preferred IUPAC name
Pyridine-2,6-dicarboxylic acid
Other names
2,6-Pyridinedicarboxylic acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.007.178 Edit this at Wikidata
  • InChI=1S/C7H5NO4/c9-6(10)4-2-1-3-5(8-4)7(11)12/h1-3H,(H,9,10)(H,11,12) checkY
    Key: WJJMNDUMQPNECX-UHFFFAOYSA-N checkY
  • InChI=1/C7H5NO4/c9-6(10)4-2-1-3-5(8-4)7(11)12/h1-3H,(H,9,10)(H,11,12)
    Key: WJJMNDUMQPNECX-UHFFFAOYAM
  • c1cc(nc(c1)C(=O)O)C(=O)O
Properties
C7H5NO4
Molar mass 167.120 g·mol−1
Melting point 248 to 250 °C (478 to 482 °F; 521 to 523 K)
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Irritant (Xi)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

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

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

  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 92724. 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

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