Chemistry:Dipicolinic acid
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| Names | |
|---|---|
| Preferred IUPAC name
Pyridine-2,6-dicarboxylic acid | |
| Other names
2,6-Pyridinedicarboxylic acid
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| Identifiers | |
3D model (JSmol)
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| 131629 | |
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| DrugBank | |
| EC Number |
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| 50798 | |
PubChem CID
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| UNII | |
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| Properties | |
| C7H5NO4 | |
| Molar mass | 167.120 g·mol−1 |
| Melting point | 248 to 250 °C (478 to 482 °F; 521 to 523 K) |
| Hazards | |
| GHS pictograms | 
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| GHS Signal word | Warning |
| H315, H319, H335 | |
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 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]
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
- ↑ 1.0 1.1 2,6-Pyridinedicarboxylic acid at Sigma-Aldrich
- ↑ "C&L Inventory". https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/34415.
- ↑ 3.0 3.1 Setlow, Peter; Nicholson, W. L. (2014). "Spore Resistance Properties". Microbiology Spectrum 2 (5): 1274–1279. doi:10.1128/microbiolspec.tbs-0003-2012. PMID 11229921. Bibcode: 2001ApEnM..67.1274S.
- ↑ 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
- [|permanent dead link|dead link}}]JPL Develops High-Speed Test to Improve Pathogen Decontamination at JPL.
- [|permanent dead link|dead link}}] Spotting Spores at Astrobiology Magazine.
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