Dipicolinic acid

Dipicolinic acid^[1]
Names
	Preferred IUPAC name Pyridine-2,6-dicarboxylic acid
	Other names 2,6-Pyridinedicarboxylic acid
Identifiers
CAS Number	499-83-2 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	131629
ChEBI	CHEBI:46837 ;
ChEMBL	ChEMBL284104 ;
ChemSpider	9940 ;
DrugBank	DB04267 ;
ECHA InfoCard	100.007.178
EC Number	207-894-3;
Gmelin Reference	50798
PubChem CID	10367;
UNII	UE81S5CQ0G ;
CompTox Dashboard (EPA)	DTXSID7022043 ;
	InChI InChI=1S/C7H5NO4/c9-6(10)4-2-1-3-5(8-4)7(11)12/h1-3H,(H,9,10)(H,11,12) Key: WJJMNDUMQPNECX-UHFFFAOYSA-N ; 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;
	SMILES c1cc(nc(c1)C(=O)O)C(=O)O;
Properties
Chemical formula	C7H5NO4
Molar mass	167.120 g·mol−1
Melting point	248 to 250 °C (478 to 482 °F; 521 to 523 K)
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

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 dipicolinato ligated lanthanide and transition metal complexes for ion chromatography.^[1]

Biological role

Dipicolinic acid composes 5% to 15% of the dry weight of Bacillus subtilis spores.^[3]^[4] It has been implicated as responsible for the heat resistance of the endospore,^[3]^[5] although mutants resistant to heat but lacking dipicolinic acid have been isolated, suggesting other mechanisms contributing to heat resistance are at work.^[6] Two genera of bacterial pathogens are known to produce endospores: the aerobic Bacillus and anaerobic Clostridium.^[7]

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.^[8]

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,^[9] although this phenomenon was first investigated for using DPA in an assay for terbium by Barela and Sherry.^[10]

Environmental behavior

Simple substituted pyridines vary significantly in environmental fate characteristics, such as volatility, adsorption, and biodegradation.^[11] Dipicolinic acid is among the least volatile, least adsorbed by soil, and most rapidly degraded of the simple pyridines.^[12] 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.^[13] 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.^[14]

References

^ ^a ^b 2,6-Pyridinedicarboxylic acid at Sigma-Aldrich
^ "C&L Inventory". echa.europa.eu. Retrieved 13 December 2021.
^ ^a ^b Setlow, Peter; Nicholson, W. L. (2014). "Spore Resistance Properties". Microbiology Spectrum. 2 (5): 1274–1279. Bibcode:2001ApEnM..67.1274S. doi:10.1128/microbiolspec.tbs-0003-2012. PMC 92724. PMID 11229921.
^ 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., ISBN 981-247-118-9.
^ Prescott, L. (1993). Microbiology, Wm. C. Brown Publishers, ISBN 0-697-01372-3.
^ Gladwin, M. (2008). Clinical Microbiology Made Ridiculously Simple, MedMaster, Inc., ISBN 0-940780-81-X.
^ 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.
^ 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.
^ 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. PMID 1275238.
^ 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.
^ 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.
^ 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
^ Anonymous. 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

^{[dead link]}JPL Develops High-Speed Test to Improve Pathogen Decontamination Archived 2016-03-04 at the Wayback Machine at JPL.
^{[dead link]} Spotting Spores at Astrobiology Magazine.

[2,6-Pyridinedicarboxylic_acid-1] 2,6-Pyridinedicarboxylic acid at Sigma-Aldrich

[2] "C&L Inventory". echa.europa.eu. Retrieved 13 December 2021.

[pyridine-3] Setlow, Peter; Nicholson, W. L. (2014). "Spore Resistance Properties". Microbiology Spectrum. 2 (5): 1274–1279. Bibcode:2001ApEnM..67.1274S. doi:10.1128/microbiolspec.tbs-0003-2012. PMC 92724. PMID 11229921.

[4] Sci-Tech Dictionary. McGraw-Hill Dictionary of Scientific and Technical Terms, McGraw-Hill Companies, Inc.

[5] Madigan, M., J Martinko, J. Parker (2003). Brock Biology of Microorganisms, 10th edition. Pearson Education, Inc., ISBN 981-247-118-9.

[6] Prescott, L. (1993). Microbiology, Wm. C. Brown Publishers, ISBN 0-697-01372-3.

[7] Gladwin, M. (2008). Clinical Microbiology Made Ridiculously Simple, MedMaster, Inc., ISBN 0-940780-81-X.

[8] 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.

[9] 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.

[10] 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. PMID 1275238.

[11] 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.

[12] 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.

[13] 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

[14] 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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Biological role

Detection

Environmental behavior

See also

References

External links