Dipicolinic acid
From Wikipedia, the free encyclopedia
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| Names | |
|---|---|
| Preferred IUPAC name
Pyridine-2,6-dicarboxylic acid | |
| Other names
2,6-Pyridinedicarboxylic acid | |
| Identifiers | |
3D model (JSmol) |
|
| 131629 | |
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| DrugBank | |
| ECHA InfoCard | 100.007.178 |
| EC Number |
|
| 50798 | |
PubChem CID |
|
| UNII | |
CompTox Dashboard (EPA) |
|
| |
| |
| 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 labelling:[2] | |
 | |
| Warning | |
| H315, H319, H335 | |
| Related compounds | |
Related compounds |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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]
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]