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EGTA

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EGTA
Skeletal formula of EGTA
Ball-and-stick model of the EGTA molecule
Names
Preferred IUPAC name
3,12-Bis(carboxymethyl)-6,9-dioxa-3,12-diazatetradecane-1,14-dioic acid
Other names
Triethylene glycol diamine tetraacetic acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.592Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C14H24N2O10/c17-11(18)7-15(8-12(19)20)1-3-25-5-6-26-4-2-16(9-13(21)22)10-14(23)24/h1-10H2,(H,17,18)(H,19,20)(H,21,22)(H,23,24)checkY
    Key: DEFVIWRASFVYLL-UHFFFAOYSA-NcheckY
  • InChI=1/C10H13NO2/c1-3-13-10-6-4-9(5-7-10)11-8(2)12/h4-7H,3H2,1-2H3,(H,11,12)
    Key: CPJSUEIXXCENMM-UHFFFAOYAO
  • InChI=1/C14H24N2O10/c17-11(18)7-15(8-12(19)20)1-3-25-5-6-26-4-2-16(9-13(21)22)10-14(23)24/h1-10H2,(H,17,18)(H,19,20)(H,21,22)(H,23,24)
    Key: DEFVIWRASFVYLL-UHFFFAOYAF
  • O=C(O)CN(CC(=O)O)CCOCCOCCN(CC(=O)O)CC(=O)O
Properties
C14H24N2O10
Molar mass 380.350g·mol−1
Melting point 241 °C (466 °F; 514 K)
Acidity(pKa) 2.0, 2.68, 8.85, 9.43[1]
Except where otherwise noted, data are given for materials in theirstandard state(at 25 °C [77 °F], 100 kPa).

EGTA(ethylene glycol-bis(β-aminoethyl ether)-N,N,N′,N′-tetraacetic acid), also known asegtazic acid(INN,USAN),[2]is anaminopolycarboxylic acid,achelating agent.It is a white solid that is related to the better knownEDTA.Compared to EDTA, it has a lower affinity formagnesium,making it more selective forcalciumions.It is useful inbuffer solutionsthat resemble the environment in livingcells[3]where calcium ions are usually at least a thousandfold less concentrated than magnesium.

ThepKafor binding of calcium ions by tetrabasic EGTA is 11.00, but theprotonated formsdo not significantly contribute to binding, so at pH 7, the apparent pKabecomes 6.91. See Qinet al.for an example of apKacalculation.[4]

EGTA has also been used experimentally for the treatment of animals withceriumpoisoning and for theseparationofthoriumfrom the mineralmonazite.EGTA is used as a compound inelutionbuffer in the protein purification technique known astandem affinity purification,in whichrecombinant fusion proteinsare bound tocalmodulinbeads and eluted out by adding EGTA.

EGTA is often employed indentistryandendodonticsfor the removal of thesmear layer.

See also

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References

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  1. ^Raaflaub, Jürg (1956)."Applications of Metal Buffers and Metal Indicators in Biochemistry".Methods of Biochemical Analysis.Vol. 3. pp. 301–325.doi:10.1002/9780470110195.ch10.ISBN978-0-470-30492-1.PMID13369167.
  2. ^Pubchem."EGTA | C14H24N2O10 - PubChem".pubchem.ncbi.nlm.nih.gov.Retrieved2017-04-24.
  3. ^Bett, Glenna C. L.; Rasmusson, Randall L. (2002). "1. Computer Models of Ion Channels". In Cabo, Candido; Rosenbaum, David S. (eds.).Quantitative Cardiac Electrophysiology.Marcel Dekker.p.48.ISBN0-8247-0774-5.
  4. ^Ning Qin; Riccardo Olcese; Michael Bransby; Tony Lin; Lutz Birnbaumer (March 1999)."Ca2+-induced inhibition of the cardiac Ca2+channel depends on calmodulin ".PNAS.96(5): 2435–2438.Bibcode:1999PNAS...96.2435Q.doi:10.1073/pnas.96.5.2435.PMC26802.PMID10051660.
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