Dipicolinic acid

Last updated
Dipicolinic acid [1]
Dipicolinic acid.png
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 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 207-894-3
50798
PubChem CID
UNII
  • InChI=1S/C7H5NO4/c9-6(10)4-2-1-3-5(8-4)7(11)12/h1-3H,(H,9,10)(H,11,12) Yes check.svgY
    Key: WJJMNDUMQPNECX-UHFFFAOYSA-N Yes check.svgY
  • 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
GHS labelling: [2]
GHS-pictogram-exclam.svg
Warning
H315, H319, H335
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

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]

Contents

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

Related Research Articles

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References

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