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Revision as of 15:46, 8 August 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,081 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'DrugBank', 'ChEBI').← Previous edit Latest revision as of 12:41, 16 July 2024 edit undoL0st H0r!z0ns (talk | contribs)Extended confirmed users1,623 editsm Undid revision 1230776492 by Mohammad9783 (talk) ''Bacillus subtilis'' according to the supporting referenceTag: Undo 
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{{chembox {{chembox
|Watchedfields = changed
| verifiedrevid = 414431743 |verifiedrevid = 443696483
|Reference=<ref> at ]</ref> |Reference=<ref name="2,6-Pyridinedicarboxylic acid"> at ]</ref>
|ImageFile=Dipicolinic acid.png |ImageFile=Dipicolinic acid.png
|ImageSize=180px |ImageSize=180px
|IUPACName=Pyridine-2,6-dicarboxylic acid |PIN = Pyridine-2,6-dicarboxylic acid
|OtherNames=2,6-Pyridinedicarboxylic acid |OtherNames = 2,6-Pyridinedicarboxylic acid
|Section1={{Chembox Identifiers |Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |CASNo_Ref = {{cascite|correct|CAS}}
⚫ |CASNo=499-83-2
⚫ | ChemSpiderID = 9940
|Beilstein = 131629
⚫ | InChI = 1/C7H5NO4/c9-6(10)4-2-1-3-5(8-4)7(11)12/h1-3H,(H,9,10)(H,11,12)
⚫ |ChEBI_Ref = {{ebicite|correct|EBI}}
⚫ | InChIKey = WJJMNDUMQPNECX-UHFFFAOYAM
| ChEMBL_Ref = {{ebicite|correct|EBI}} |ChEBI = 46837
|ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 284104 |ChEMBL = 284104
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
⚫ |ChemSpiderID = 9940
⚫ | StdInChI = 1S/C7H5NO4/c9-6(10)4-2-1-3-5(8-4)7(11)12/h1-3H,(H,9,10)(H,11,12)
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |DrugBank_Ref = {{drugbankcite|correct|drugbank}}
⚫ |DrugBank = DB04267
⚫ | StdInChIKey = WJJMNDUMQPNECX-UHFFFAOYSA-N
|EINECS = 207-894-3
⚫ | CASNo_Ref = {{cascite|correct|CAS}}
|Gmelin = 50798
⚫ | CASNo=499-83-2
| PubChem=10367 |PubChem=10367
|UNII_Ref = {{fdacite|correct|FDA}}
⚫ | DrugBank = DB04267
|UNII = UE81S5CQ0G
| ChEBI = 46837
⚫ |InChI = 1/C7H5NO4/c9-6(10)4-2-1-3-5(8-4)7(11)12/h1-3H,(H,9,10)(H,11,12)
⚫ | SMILES = c1cc(nc(c1)C(=O)O)C(=O)O
⚫ |InChIKey = WJJMNDUMQPNECX-UHFFFAOYAM
|StdInChI_Ref = {{stdinchicite|correct|chemspider}}
⚫ |StdInChI = 1S/C7H5NO4/c9-6(10)4-2-1-3-5(8-4)7(11)12/h1-3H,(H,9,10)(H,11,12)
|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
⚫ |StdInChIKey = WJJMNDUMQPNECX-UHFFFAOYSA-N
⚫ |SMILES = c1cc(nc(c1)C(=O)O)C(=O)O
}} }}
|Section2={{Chembox Properties |Section2={{Chembox Properties
|C=7 | H=5 | N=1 | O=4
| Formula=C<sub>7</sub>H<sub>5</sub>NO<sub>4</sub>
|MeltingPtC=248 to 250
| MolarMass=167.1189
⚫ }}
| Appearance=
| Density=
| MeltingPt=248-250 °C
| BoilingPt=
| Solubility=
⚫ }}
|Section3={{Chembox Hazards |Section3={{Chembox Hazards
|GHS_ref=<ref>{{cite web |title=C&L Inventory |url=https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/34415 |website=echa.europa.eu |access-date=13 December 2021}}</ref>
| MainHazards=Irritant ('''Xi''')
|GHSPictograms = {{GHS07}}
| FlashPt=
|GHSSignalWord = Warning
| Autoignition=
| RPhrases = {{R36/37/38}} |HPhrases = {{H-phrases|315|319|335}}
| SPhrases = {{S26}} {{S36}} |PPhrases = {{P-phrases|}}
}} }}
}} }}


'''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 ] and ] ] for ion ].<ref name="2,6-Pyridinedicarboxylic acid"> at ]</ref>
'''Dipicolinic acid''' (pyridine-2,6-dicarboxylic acid or '''PDC''') is a chemical compound which composes 5% to 15% of the dry weight of ]l spores.<ref name="pyridine">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</ref><ref>Sci-Tech Dictionary. ''McGraw-Hill Dictionary of Scientific and Technical Terms'', McGraw-Hill Companies, Inc.</ref> It is implicated as responsible for the heat resistance of the ].<ref name="pyridine"/><ref>Madigan, M., J Martinko, J. Parker (2003). ''Brock Biology of Microorganisms'', 10th edition. Pearson Education, Inc., ISBN 981-247-118-9.</ref>


== Biological role ==
However, mutants resistant to heat but lacking dipicolinic acid have been isolated, suggesting other mechanisms contributing to heat resistance are at work.<ref>Prescott, L. (1993). ''Microbiology'', Wm. C. Brown Publishers, ISBN 0-697-01372-3.</ref>
Dipicolinic acid composes 5% to 15% of the dry weight of '']'' spores.<ref name="pyridine">{{cite journal|doi=10.1128/microbiolspec.tbs-0003-2012
|pmc=92724|pmid=11229921|bibcode=2001ApEnM..67.1274S
|title=Spore Resistance Properties
|year=2014
|last1=Setlow
|first1=Peter
|last2=Nicholson
|first2=W. L.
|journal=Microbiology Spectrum
|volume=2
|issue=5
|pages=1274–1279
}}</ref><ref>Sci-Tech Dictionary. ''McGraw-Hill Dictionary of Scientific and Technical Terms'', McGraw-Hill Companies, Inc.</ref> It has been implicated as responsible for the heat resistance of the ],<ref name="pyridine" /><ref>Madigan, M., J Martinko, J. Parker (2003). ''Brock Biology of Microorganisms'', 10th edition. Pearson Education, Inc., {{ISBN|981-247-118-9}}.</ref> although mutants resistant to heat but lacking dipicolinic acid have been isolated, suggesting other mechanisms contributing to heat resistance are at work.<ref>Prescott, L. (1993). ''Microbiology'', Wm. C. Brown Publishers, {{ISBN|0-697-01372-3}}.</ref> Two genera of bacterial pathogens are known to produce endospores: the aerobic '']'' and anaerobic '']''.<ref>Gladwin, M. (2008). ''Clinical Microbiology Made Ridiculously Simple'', MedMaster, Inc., {{ISBN|0-940780-81-X}}.</ref>


Dipicolinic acid forms a complex with ] 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 ] from heat denaturation by inserting itself between the ], thereby increasing the stability of DNA.<ref>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}}.</ref>
Two genera of bacteria are known to produce endospores: the aerobic ] and anaerobic ].<ref>Gladwin, M. (2008). ''Clinical Microbiology Made Ridiculously Simple'', MedMaster, Inc., ISBN 0-940780-81-X.</ref>


==Detection==
A Jet Propulsion Laboratory chemist has developed technology to perform high speed, large area assessments of sterilization by searching for dipicolinic acid as an indicator of spores, being the hardiest of life forms. ] can more rapidly be ascertained, as well as the sterility of medical equipment and facilities.{{Citation needed|date=September 2010}}
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 ] in the presence of ],<ref>{{cite journal|last1=Rosen|first1=D.L.|last2=Sharpless|first2=C.|last3=McGown|first3=L.B.|title=Bacterial Spore Detection and Determination by Use of Terbium Dipicolinate Photoluminescence|journal=Analytical Chemistry|date=1997|volume=69|issue=6|pages=1082–1085|doi=10.1021/ac960939w}}</ref> although this phenomenon was first investigated for using DPA in an assay for terbium by Barela and Sherry.<ref>{{cite journal|last1=Barela|first1=T.D.|last2=Sherry|first2=A.D.|title=A simple, one step fluorometric method for determination of nanomolar concentrations of terbium|journal=Analytical Biochemistry|date=1976|volume=71|issue=2|pages=351–357|doi=10.1016/s0003-2697(76)80004-8|pmid=1275238}}</ref>

==Environmental behavior==
Simple substituted ] vary significantly in environmental fate characteristics, such as ], ], and ].<ref>{{cite journal | last1 = Sims | first1 = G. K. | last2 = O'Loughlin | first2 = E.J. | year = 1989 | title = Degradation of pyridines in the environment | journal = CRC Critical Reviews in Environmental Control | volume = 19 | issue = 4| pages = 309–340 | doi = 10.1080/10643388909388372 }}</ref> Dipicolinic acid is among the least volatile, least adsorbed by soil, and most rapidly degraded of the simple pyridines.<ref>{{cite journal | last1 = Sims | first1 = G. K. | last2 = Sommers | first2 = L.E. | year = 1986 | title = Biodegradation of pyridine derivatives in soil suspensions | journal = Environmental Toxicology and Chemistry | volume = 5 | issue = 6| pages = 503–509 | doi = 10.1002/etc.5620050601 }}</ref> A number of studies have confirmed dipicolinic acid is biodegradable in ] and ] environments, which is consistent with the widespread occurrence of the compound in nature.<ref>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}}</ref> 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 ] in nature.<ref>Anonymous. MSDS. pyridine-2-6-carboxylic-acid .Jubilant Organosys Limited. http://www.jubl.com/uploads/files/39msds_msds-pyridine-2-6-carboxylic-acid.pdf</ref>

==See also==
* ], an isomeric dicarboxylic acid
* ] has both -COOH (]) groups replaced by -COSH (]) groups


==References== ==References==
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==External links== ==External links==
* at ]. * {{deadlink|date=October 2023}} {{Webarchive|url=https://web.archive.org/web/20160304230517/http://www.nasa.gov/topics/technology/features/endospore20091019.html |date=2016-03-04 }} at ].
* at Astrobiology Magazine. * {{deadlink|date=October 2023}} at Astrobiology Magazine.


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