Dipicolinic Acid Synthesis Essay

Names
Preferred IUPAC name

Pyridine-2,6-dicarboxylic acid

Other names

2,6-Pyridinedicarboxylic acid

Identifiers

CAS Number

3D model (JSmol)

ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard100.007.178

PubChemCID

InChI

  • InChI=1S/C7H5NO4/c9-6(10)4-2-1-3-5(8-4)7(11)12/h1-3H,(H,9,10)(H,11,12) Y
    Key: WJJMNDUMQPNECX-UHFFFAOYSA-N Y
  • 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

Properties

Chemical formula

C7H5NO4
Molar mass167.12 g·mol−1
Melting point248 to 250 °C (478 to 482 °F; 521 to 523 K)
Hazards
Main hazardsIrritant (Xi)
R-phrases(outdated)R36/37/38
S-phrases(outdated)S26S36

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Y verify (what is YN ?)
Infobox references

Dipicolinic acid (pyridine-2,6-dicarboxylic acid or PDC and DPA) is a chemical compound which composes 5% to 15% of the dry weight of bacterial spores.[2][3] It is implicated as responsible for the heat resistance of the endospore.[2][4]

However, mutants resistant to heat but lacking dipicolinic acid have been isolated, suggesting other mechanisms contributing to heat resistance are at work.[5]

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.[6]

Two genera of bacterial pathogens are known to produce endospores: the aerobic Bacillus and anaerobic Clostridium.[7]

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,[8] though ironically this phenomenon was first investigated for using DPA in an assay for terbium by Barela and Sherry.[9] Extensive subsequent work by numerous scientists has elaborated on and further developed this approach.

It is also used to prepare dipicolinato ligated lanthanide and transition metalcomplexes for ion chromatography.[1]

Environmental behavior[edit]

Simple substituted pyridines vary significantly in environmental fate characteristics, such as volatility, adsorption, and biodegradation.[10] Dipicolinic acid is among the least volatile, least adsorbed by soil, and most rapidly degraded of the simple pyridines.[11] 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.[12] 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.[13]

References[edit]

External links[edit]

  1. ^ ab2,6-Pyridinedicarboxylic acid at Sigma-Aldrich
  2. ^ abSliemandagger, 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. doi:10.1128/aem.67.3.1274-1279.2001. PMC 92724. PMID 11229921. 
  3. ^Sci-Tech Dictionary. McGraw-Hill Dictionary of Scientific and Technical Terms, McGraw-Hill Companies, Inc.
  4. ^Madigan, M., J Martinko, J. Parker (2003). Brock Biology of Microorganisms, 10th edition. Pearson Education, Inc., ISBN 981-247-118-9.
  5. ^Prescott, L. (1993). Microbiology, Wm. C. Brown Publishers, ISBN 0-697-01372-3.
  6. ^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.
  7. ^Gladwin, M. (2008). Clinical Microbiology Made Ridiculously Simple, MedMaster, Inc., ISBN 0-940780-81-X.
  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. 
  9. ^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. 
  10. ^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. 
  11. ^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. 
  12. ^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
  13. ^Annonymous. MSDS. pyridine-2-6-carboxylic-acid .Jubilant Organosys Limited. http://www.jubl.com/uploads/files/39msds_msds-pyridine-2-6-carboxylic-acid.pdf

Abstract

Some of the early enzymes in the lysine-biosynthetic pathway also function for dipicolinic acid synthesis in sporulating Bacillus cereus T. 1. The first enzyme, aspartokinase, loses its sensitivity to feedback inhibition by lysing. This change occurs before the time of dipicolinic acid synthesis but at a time when diaminopimelic acid is required for spore cortex formation. 2. A possible regulatory change at a branch point in the pathway was studied by examining the properties of a key enzyme, dihydrodipicolinic acid reductase. No alteration in the feedback sensitivity or sedimentation rate of this enzyme could be detected during sporulation. 3. Two mutants producing heat-sensitive spores were analysed. Both produced spores that contained decreased amounts of dipicolinic acid. Although neither was a lysine auxotroph, they both had greatly decreased activities of certain lysine-biosynthetic enzymes in sporulating cells. 4. Starvation of cells for calcium also results in the production of spores that are heat-sensitive and contain less dipicolinic acid than the control. A decreased content of one of the lysine-biosynthetic enzymes, dihydrodipicolinic acid synthetase, in calcium-starved cells could account for the lower concentration of dipicolinic acid in the spores.

Full text

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Selected References

These references are in PubMed. This may not be the complete list of references from this article.
  • Aronson AI, Henderson E, Tincher A. Participation of the lysine pathway in dipicolinic acid synthesis in Bacillus cereus T. Biochem Biophys Res Commun. 1967 Feb 21;26(4):454–460.[PubMed]
  • Bach ML, Gilvarg C. Biosynthesis of dipicolinic acid in sporulating Bacillus megaterium. J Biol Chem. 1966 Oct 10;241(19):4563–4564.[PubMed]
  • BLACK S, WRIGHT NG. Aspartic beta-semialdehyde dehydrogenase and aspartic beta-semialdehyde. J Biol Chem. 1955 Mar;213(1):39–50.[PubMed]
  • BLACK SH, HASHIMOTO T, GERHARDT P. Calcium reversal of the heat susceptibility and dipicolinate deficiency of spores formed "endotrophically" in water. Can J Microbiol. 1960 Apr;6:213–224.[PubMed]
  • Bukhari AI, Taylor AL. Genetic analysis of diaminopimelic acid- and lysine-requiring mutants of Escherichia coli. J Bacteriol. 1971 Mar;105(3):844–854.[PMC free article][PubMed]
  • Dvorak HF. Metallo-enzymes released from Escherichia coli by osmotic shock. I. Selective depression of enzymes in cells grown in the presence of ethylenediaminetetraacetate. J Biol Chem. 1968 May 25;243(10):2640–2646.[PubMed]
  • Farkas W, Gilvarg C. The reduction step in diaminopimelic acid biosynthesis. J Biol Chem. 1965 Dec;240(12):4717–4722.[PubMed]
  • Fish WW, Mann KG, Tanford C. The estimation of polypeptide chain molecular weights by gel filtration in 6 M guanidine hydrochloride. J Biol Chem. 1969 Sep 25;244(18):4989–4994.[PubMed]
  • Fukuda A, Gilvarg C. The relationship of dipicolinate and lysine biosynthesis in Bacillus megaterium. J Biol Chem. 1968 Jul 25;243(14):3871–3876.[PubMed]
  • GOLLAKOTA KG, HALVORSON HO. Biochemical changes occurring during sporulation of Bacillus cereus. Inhibition of sporulation by alpha-picolinic acid. J Bacteriol. 1960 Jan;79:1–8.[PMC free article][PubMed]
  • Grandgenett DP, Stahly DP. Diaminopimelate decarboxylase of sporulating bacteria. J Bacteriol. 1968 Dec;96(6):2099–2109.[PMC free article][PubMed]
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