Acceleration of a Phosphate Diester Transesterification Reaction by Bis(alkylguanidinium) Receptors Containing an Appended General Base

Vrej Jubian, Andrea Veronese, Robert P. Dixon, Andrew D. Hamilton

Research output: Contribution to journalArticle

Abstract

Rate enhancements up to 290‐fold are possible for the transesterification of 2‐hydroxypropyl‐p‐nitrophenylphosphate when bis(guanidinium) catalysts bearing basic groups are added. The combination of the appended base and the electrostatic complementarity of substrate and receptor (see complex 1) make the guanidinium compounds efficient enzyme mimics. These types of compounds may have therapeutic applications as artificial nucleases. (Figure Presented.)

Original languageEnglish (US)
Pages (from-to)1237-1239
Number of pages3
JournalAngewandte Chemie International Edition in English
Volume34
Issue number11
DOIs
StatePublished - Jun 16 1995

Keywords

  • enzyme mimics
  • guanidines
  • transesterifications

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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