Bioconjugation with Thiols by Benzylic Substitution

Kenji Watanabe, Takashi Ohshima

Research output: Contribution to journalArticlepeer-review

6 Citations (Scopus)


A benzylic substitution of 3-indolyl(hydroxyl)acetate derivatives with thiols proceeded specifically in the presence of amino, carboxy, and phosphate groups in weakly acidic aqueous solutions under nearly physiological condition, while no reaction occurred at pH over 7. Kinetic studies revealed that the reaction followed second-order kinetics (first-order in the reactant and first-order in thiol) in contrast with the SN1 mechanism of common benzylic substitution of alcohols. The utility of the present method for functionalization of biomacromolecules was demonstrated using several model proteins, such as lysozyme, insulin, trypsin, and serum albumin. The catalytic bioactivity of lysozyme in lysis of Micrococcus lysodeikticus cells was completely retained after the modification.

Original languageEnglish
Pages (from-to)3959-3964
Number of pages6
JournalChemistry - A European Journal
Issue number16
Publication statusPublished - Mar 15 2018

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Organic Chemistry


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