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Nitrilotriacetic acid

2-[Bis(carboxymethyl)amino]acetic acid Triglycine Trilon

Nitrilotriacetic acid (NTA) is the aminopolycarboxylic acid with the formula N(CH2CO2H)3. It is a colourless solid. Its conjugate base nitrilotriacetate is used as a chelating agent for Ca2+, Co2+, Cu2+, and Fe3+.

Production and use

Nitrilotriacetic acid is commercially available as the free acid and as the sodium salt. It is produced from ammonia, formaldehyde, and sodium cyanide or hydrogen cyanide. NTA is also cogenerated as an impurity in the synthesis of EDTA, arising from reactions of the ammonia coproduct. Older routes to NTA included alkylation of ammonia with chloroacetic acid and oxidation of triethanolamine.

Coordination chemistry and applications

The conjugate base of NTA is a tripodal tetradentate trianionic ligand, forming coordination compounds with a variety of metal ions.

Like EDTA, its sodium salt is used for water softening to remove Ca2+. For this purpose, NTA is a replacement for triphosphate, which once was widely used in detergents, and cleansers, but can cause eutrophication of lakes.

In one application, sodium NTA removes Cr, Cu, and As from wood that had been treated with chromated copper arsenate.

Laboratory uses

In the laboratory, this compound is used in complexometric titrations. A variant of NTA is used for protein isolation and purification in the His-tag method. The modified NTA is used to immobilize nickel on a solid support. This allows purification of proteins containing a tag consisting of six histidine residues at either terminus.

The His-tag binds the metal of metal chelator complexes. Previously, iminodiacetic acid was used for that purpose. Now, nitrilotriacetic acid is more commonly used.

For laboratory uses, Ernst Hochuli et al. (1987) coupled the NTA ligand and nickel ions to agarose beads. This Ni-NTA Agarose is the most used tool to purify His-tagged proteins via affinity chromatography. Ni(NTA)(aq)23views.png|Three views of the structure of [Ni(NTA)(H2O)2]−. File:Calcium complex of NTA trianion.svg|Structure of the nitrilotriacetate anion [Ca(NTA)(H2O)3]−.

Toxicity and environment

In contrast to EDTA, NTA is easily biodegradable and is almost completely removed during wastewater treatment.

References

References

  1. (2014). "Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 (Blue Book)". [[Royal Society of Chemistry.
  2. (26 March 2005). "Nitrilotriacetic Acid - Compound Summary". National Center for Biotechnology Information.
  3. [http://www.chemspider.com/8428 Nitrilotriacetic acid]
  4. [http://www.inchem.org/documents/iarc/vol48/48-12.html Nitrilotriacetic Acid and Its Salts], International Agency for Research on Cancer
  5. (2022). "Nitrilotriacetic Acid".
  6. (15 June 2000). "Ethylenediaminetetraacetic Acid and Related Chelating Agents". Ullmann's Encyclopedia of Industrial Chemistry.
  7. (1 October 1979). "Structural investigations of calcium-binding molecules. 4. Calcium binding to aminocarboxylates. Crystal structures of Ca(CaEDTA). 7H2O and Na(CaNTA)". Inorganic Chemistry.
  8. (June 2013). "Factors affecting chelating extraction of Cr, Cu, and As from CCA-treated wood". Journal of Environmental Management.
  9. (2016). "Layer-by-Layer Deposition with Polymers Containing Nitrilotriacetate, A Convenient Route to Fabricate Metal- and Protein-Binding Films". ACS Applied Materials & Interfaces.
  10. [http://www1.qiagen.com/literature/handbooks/PDF/Protein/Expression/QXP_QIAexpressionist/1024473_QXPHB_0603.pdf qiaexpressionist]
  11. (2002). "Development and characterization of Ni-NTA-bearing microspheres". Cytometry.
  12. (January 1987). "New metal chelate adsorbent selective for proteins and peptides containing neighbouring histidine residues". Journal of Chromatography A.
  13. (May 1995). "Ecological and toxicological properties of nitrilotriacetic acid (NTA) as a detergent builder". Tenside Surfactants Detergents.
  14. (2007). "Stabilizing Factors for Vanadium(IV) in Amavadin". European Journal of Organic Chemistry.
  15. "Nitrilotriacetic acid".
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amines acetic-acids chelating-agents iarc-group-2b-carcinogens tripodal-ligands
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