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Amine-Reactive Reagents

  • Engelbert Buxbaum
Chapter

Abstract

Aliphatic amines ( ε -amino group of Lys) are moderately nucleophilic when deprotonated (beyond pH 9 for the free amino acid, but often much lower in proteins); on the other hand, the inactivation of the labelling reagent by water increases with pH. The α -amino group has a pKa of 7. 6–8. 5, thus the N-terminus of a protein can be labelled specifically around pH 7. Aromatic amines require very reactive probes (thiocyanate, sulphonyl chloride), but can be labelled at any pH > 4. The nitrogen of peptide bonds and Gln, Asn, Arg and His side-chains, and of guanosine and adenosine are almost unreactive. Amino-sugars in glycoproteins may also react.

Keywords

Aromatic Amine Aliphatic Amine Cyanogen Bromide Pyridoxal Phosphate Dansyl Chloride 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Copyright information

© Springer Science+Business Media, LLC 2011

Authors and Affiliations

  1. 1.BiochemistryRoss University School of MedicineRoseauDominica

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