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 metalcomplexes for ion chromatography.[1]
Dipicolinic acid composes 5% to 15% of the dry weight of bacterial 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]
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] Extensive subsequent work by numerous scientists has elaborated on and further developed this approach.
Environmental behavioredit
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]
^"C&L Inventory". echa.europa.eu. Retrieved 13 December 2021.
^ abSetlow, Peter; Nicholson, W. L. (2014). "Spore Resistance Properties". Microbiology Spectrum. 2 (5): 1274–1279. Bibcode:2001ApEnM..67.1274S. doi:10.1128/microbiolspec.tbs-0003-2012. PMC92724. PMID 11229921.
^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., ISBN981-247-118-9.
^Prescott, L. (1993). Microbiology, Wm. C. Brown Publishers, ISBN0-697-01372-3.
^Gladwin, M. (2008). Clinical Microbiology Made Ridiculously Simple, MedMaster, Inc., ISBN0-940780-81-X.
^Madigan. M, Martinko. J, Bender. K, Buckley. D, Stahl. D, (2014), Brock Biology of Microorganisms, 14th Edition, p. 78, Pearson Education Inc., ISBN978-0-321-89739-8.
^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
[dead link]JPL Develops High-Speed Test to Improve Pathogen Decontamination at JPL.
[dead link] Spotting Spores at Astrobiology Magazine.
November 23, 2023
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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 1 NamesPreferred IUPAC name Pyridine 2 6 dicarboxylic acidOther names 2 6 Pyridinedicarboxylic acidIdentifiersCAS Number 499 83 2 Y3D model JSmol Interactive imageBeilstein Reference 131629ChEBI CHEBI 46837 YChEMBL ChEMBL284104 YChemSpider 9940 YDrugBank DB04267 YECHA InfoCard 100 007 178EC Number 207 894 3Gmelin Reference 50798PubChem CID 10367UNII UE81S5CQ0G YCompTox Dashboard EPA DTXSID7022043InChI InChI 1S C7H5NO4 c9 6 10 4 2 1 3 5 8 4 7 11 12 h1 3H H 9 10 H 11 12 YKey WJJMNDUMQPNECX UHFFFAOYSA N YInChI 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 UHFFFAOYAMSMILES c1cc nc c1 C O O C O OPropertiesChemical formula C 7H 5N O 4Molar mass 167 120 g mol 1Melting point 248 to 250 C 478 to 482 F 521 to 523 K HazardsGHS labelling 2 PictogramsSignal word WarningHazard statements H315 H319 H335Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Y verify what is Y N Infobox references Contents 1 Biological role 2 Environmental behavior 3 See also 4 References 5 External linksBiological role editDipicolinic acid composes 5 to 15 of the dry weight of bacterial 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 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 Extensive subsequent work by numerous scientists has elaborated on and further developed this approach Environmental behavior editSimple 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 editDinicotinic acid an isomeric dicarboxylic acid 2 6 Pyridinedicarbothioic acid has both COOH carboxylic acid groups replaced by COSH thiocarboxylic acid groupsReferences edit a b 2 6 Pyridinedicarboxylic acid at Sigma Aldrich C amp L Inventory echa europa eu Retrieved 13 December 2021 a b Setlow Peter Nicholson W L 2014 Spore Resistance Properties Microbiology Spectrum 2 5 1274 1279 Bibcode 2001ApEnM 67 1274S doi 10 1128 microbiolspec tbs 0003 2012 PMC 92724 PMID 11229921 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 pdfExternal links edit dead link JPL Develops High Speed Test to Improve Pathogen Decontamination at JPL dead link Spotting Spores at Astrobiology Magazine Retrieved from https en wikipedia org w index php title Dipicolinic acid amp oldid 1178328108, wikipedia, wiki, book, books, library,
