Bioconjugation with Thiols by Benzylic Substitution

Kenji Watanabe, Takashi Ohshima

研究成果: Contribution to journalArticle査読

2 被引用数 (Scopus)

抄録

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.

本文言語英語
ページ(範囲)3959-3964
ページ数6
ジャーナルChemistry - A European Journal
24
16
DOI
出版ステータス出版済み - 3 15 2018

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Organic Chemistry

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