Single electron transfer-based peptide/protein bioconjugations driven by biocompatible energy input

Abstract

Bioconjugation reactions play a central facilitating role in engendering modified peptides and proteins. Early progress in this area was inhibited by challenges such as the limited range of substrates and the relatively poor biocompatibility of bioconjugation reagents. However, the recent developments in visible-light induced photoredox catalysis and electrochemical catalysis reactions have permitted significant novel reactivities to be developed in the field of synthetic and bioconjugation chemistry. This perspective describes recent advances in the use of biocompatible energy input for the modification of peptides and proteins mainly, via the single electron transfer (SET) process, as well as key future developments in this area.

Organic Electrochemistry: Molecular Syntheses with Potential

“…In summary, electrosynthesis offers a green platform with the prospect for sustainable molecular synthesis for peptide chemistry, 132 biochemistry, 133 and material sciences. 134 Furthermore, the ideal levels of resource economy of electrochemistry hold great potential for large-scale industrial manufacturing.…”

Metal‐Catalyzed C(sp2)−H Functionalization Processes of Phenylalanine‐ and Tyrosine‐Containing Peptides

“…Third, huge number of chemical oxidants and additives are often required, thus diminishing the sustainability of the protocols. In this respect, emerging trends such as the use of electricity could offer attractive opportunities for achieving biocompatible labelling reactions, [67] thereby avoiding the use of chemical oxidants and byproducts derived thereof. Finally, owing to the chemical versatility of the resulting products, the development of new reactions to install heteroatom‐containing motifs into the peptide template represents a task of prime importance.…”

Protein Chemical Modification Using Highly Reactive Species and Spatial Control of Catalytic Reactions

“…Gouin and colleagues succeeded in suppressing the side reaction by electrochemically generating PTAD from phenylurazole in situ. 50) In addition to nucleophilic reactions, approaches using radical reactions using oxidants, 11,51) enzymes, [52][53][54][55][56] photoredox catalysts, [57][58][59][60] and electrochemistry [61][62][63] have been reported.…”