Nitrilotriacetic acid

Nitrilotriacetic acid
Skeletal formula of nitrilotriacetic acid
IUPAC name 2,2',2''-nitrilotriacetic acid
style="background: #F8EABA; text-align: center;" colspan="2" | Identifiers
CAS number	139-13-9 Y
PubChem	8758
SMILES
style="background: #F8EABA; text-align: center;" colspan="2" | Properties
Molecular formula	C6H9NO6
Molar mass	191.14 g mol−1
Y (what is this?)  (verify) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Nitrilotriacetic acid (NTA), C₆H₉NO₆, is a polyamino carboxylic acid and is used as a chelating agent which forms coordination compounds with metal ions (chelates) such as Ca²⁺, Cu²⁺ or Fe³⁺.

The uses of NTA are similar to that of EDTA. However, in contrast to EDTA, NTA is easily biodegradable and is almost completely removed during wastewater treatment.

In biotechnology applications it is used for protein isolation and purification. An aminobutanylated variant of NTA, called bis(carboxylmethyl)lysine, is linked to sephadex, which is used as a gel for affinity column chromatography. Because the nucleophilic nitrogen of imidazole (i.e. the Histidine side chain) can coordinate nickel cations, recombinant proteins containing a His-tag — 6 histidine residues at the C-terminus — will bind to the gel, while other proteins will not. After extensive washing to remove unbound protein, the tagged proteins are released by competition with a high concentration of imidazole.

References

cs:Nitrilotrioctová kyselina pt:Ácido nitrilotriacético