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Protein labeling by reductive methylation with sodium cyano borohydride effect of cyanide and metal ions on the reaction



Protein labeling by reductive methylation with sodium cyano borohydride effect of cyanide and metal ions on the reaction



Analytical Biochemistry 106(1): 186-190



Previous studies demonstrated that reductive methylation with labeled formaldehyde and NaCNBH3 provides a simple method for specifically labeling the amino groups of proteins using extremely mild reaction conditions. Cyanide, which is one of the products of the reaction, reduces labeling efficiency to reacting with formaldehyde to form the formaldehyde cyanohydrin addition product. Certain transition metal ions are able to prevent this secondary reaction by forming stable coordination complexes with cyanide. Inclusion of millimolar quantities of Ni(II) in reaction mixtures leads to a 20-30% increase in protein labeling so that maximal derivatization of amino groups can be realized with only a 3- to 4-fold ratio of formaldehyde to amine rather than the 5- to 10-fold excess necessary in the absence of metal ions.

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Accession: 006212207

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PMID: 7416460


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