Electrochemical chemoselective hydroxyl group transformation: anthranilic acyl modification of tyrosine bioconjugations

Abstract

Herein, we report an electrochemically promoted chemoselective hydroxyl group transformation for accessing of tyrosine-contained biomolecules with valuable anthranilic acid derivatives. Notably, this method utilizes fluoride anion as electrolyte and hydrogen-bonding...

Electrochemical and photochemical reaction of isatins: a decade update

“…In 2023, Weng and Gao's group 22 reported electrochemical chemo-selective transformations of isatins to anthranilic acid derivatives (Scheme 16). They reacted isatins ( 1a ) with tyrosine-containing biomolecules ( 20 ) to obtain the desired modified tyrosine products ( 21 ) in the presence of n -Bu 4 NF·3H 2 O as electrolyte and MeCN as a solvent, with an electrochemical setup of a platinum plate as the anode and a lead plate as the cathode (Scheme 16).…”

Electrochemical synthesis of peptide aldehydes via C‒N bond cleavage of cyclic amines

“…As a mild and customizable reaction platform 34 , electrochemistry offers great promise in overcoming the chemo- and regioselectivity issues encountered in conventional bioconjugation strategies 35 – 39 . Recent contributions in electrochemical modification of peptides were mainly achieved by tyrosine- 40 – 45 and tryptophan- 46 , 47 specific functionalization as well as side chain diversification via direct or indirect electrochemical methods. Recognizing the necessity for additional research methodologies to facilitate the coupling of specific functional groups, various structural functionalization reactions of cyclic amines 48 were initiated, in order to access distinctive chemical and functional spaces.…”