Dipicolinic acid
 | |
| Names | |
|---|---|
| IUPAC name
Pyridine-2,6-dicarboxylic acid | |
| Other names
2,6-Pyridinedicarboxylic acid | |
| Identifiers | |
499-83-2  | |
| ChEBI | CHEBI:46837 |
| ChEMBL | ChEMBL284104 |
| ChemSpider | 9940 |
| DrugBank | DB04267 |
| Jmol 3D model | Interactive image |
| PubChem | 10367 |
| |
| |
| 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.[10]
References
- ↑ 2,6-Pyridinedicarboxylic acid at Sigma-Aldrich
- 1 2 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.
- ↑ 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.
- ↑ 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.
- ↑ Gladwin, M. (2008). Clinical Microbiology Made Ridiculously Simple, MedMaster, Inc., ISBN 0-940780-81-X.
- ↑ 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.
- ↑ 2,6-Pyridinedicarboxylic acid at Sigma-Aldrich
External links
- JPL Develops High-Speed Test to Improve Pathogen Decontamination at JPL.
- Spotting Spores at Astrobiology Magazine.