Modification of amino groups

Current Protocols in Protein Science
K F Geoghegan

Abstract

This unit describes group-specific modifications of amino groups. These reactions remain valid tools for early-stage evaluation of structure-function relationships, but are now valued even more for their applications in the preparation of bioconjugates, affinity columns, biosensors, and tagged macromolecules. Protocols are provided here for reaction of amino groups with succinimidyl esters and isothiocyanates. These methods are broadly useful for the stable coupling to proteins of groups with useful, non-native functional properties. These include biotin for detection or recovery, fluorescent groups for biophysics or cytochemistry, cross-linking reagents for making bioconjugates, or metal-chelators that permit proteins to be loaded with radioisotopes for medical imaging or antitumor therapy. These applications require accurate product characterization, which preferably is performed by mass spectrometry, as described in this unit as a support procedure. A protocol employing succinic or acetic anhydrides to change the charge state of protein amino groups is provided here, as is a procedure for reductive alkylation that leaves their charge unaltered but converts primary amines to secondary or tertiary amines.

References

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Citations

Jan 5, 2017·Journal of Proteome Research·Vahid GolghalyaniMichael Karas
Jun 22, 2007·Molecular Microbiology·J Alfredo BonillaJohn B Dame
Apr 4, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Kunal N MoreDong-Jo Chang
Apr 25, 2008·Current Protocols in Immunology·Gregory A Grant

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