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. 2011 May 21;47(19):5452-4.
doi: 10.1039/c1cc11114k. Epub 2011 Apr 5.

Tunable reagents for multi-functional bioconjugation: reversible or permanent chemical modification of proteins and peptides by control of maleimide hydrolysis

Chris P Ryan  1 , Mark E B Smith, Felix F Schumacher, Dina Grohmann, Danai Papaioannou, Gabriel Waksman, Finn Werner, James R Baker, Stephen Caddick
Affiliations

Tunable reagents for multi-functional bioconjugation: reversible or permanent chemical modification of proteins and peptides by control of maleimide hydrolysis

Chris P Ryan et al. Chem Commun (Camb). .

Abstract

Controlling maleimide hydrolysis allows the modular construction of bromomaleimide-mediated bioconjugates which are either stable or cleavable in an aqueous, thiol-mediated reducing environment. The application of this methodology to reversible protein biotinylation, the irreversible labeling of peptide disulfide bonds and the assembly of stable, fluorescein-labelled glycoprotein mimics is described.

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Figures

Scheme 1
Scheme 1. From reversible to irreversible protein modification with N-phenylbromomaleimide.
Scheme 2
Scheme 2. Irreversible protein bioconjugation using N-phenyl-dibromomaleimide.
Scheme 3
Scheme 3. Cleavable biotinylation of protein 1 with affinity tag 11.
Scheme 4
Scheme 4. Reversible and irreversible fluorescent labelling of somatostatin.
Scheme 5
Scheme 5. Non-cleavable, fluorescent glycoprotein mimic.
See this image and copyright information in PMC

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