Dipicolinic acid

Source: Wikipedia, the free encyclopedia.
Dipicolinic acid[1]
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 Edit this at Wikidata
EC Number
  • 207-894-3
50798
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) checkY
    Key: WJJMNDUMQPNECX-UHFFFAOYSA-N checkY
  • 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]
GHS07: Exclamation mark
Warning
H315, H319, H335
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

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

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

References

  1. ^ a b 2,6-Pyridinedicarboxylic acid at Sigma-Aldrich
  2. ^ "C&L Inventory". echa.europa.eu. Retrieved 13 December 2021.
  3. ^
    PMID 11229921
    .
  4. ^ Sci-Tech Dictionary. McGraw-Hill Dictionary of Scientific and Technical Terms, McGraw-Hill Companies, Inc.
  5. ISBN 981-247-118-9
    .
  6. ISBN 0-697-01372-3
    .
  7. ISBN 0-940780-81-X
    .
  8. ISBN 978-0-321-89739-8
    .
  9. doi:10.1021/ac960939w
    .
  10. PMID 1275238
    .
  11. doi:10.1080/10643388909388372
    .
  12. doi:10.1002/etc.5620050601
    .
  13. 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

External links

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