Induced-fit catalysis of corannulene bowl-to-bowl inversion

Michal Juríček, Nathan L. Strutt, Jonathan C. Barnes, Anna M. Butterfield, Edward J. Dale, Kim K. Baldridge, J. Fraser Stoddart, Jay S. Siegel

Research output: Contribution to journalArticlepeer-review

97 Scopus citations

Abstract

Stereoelectronic complementarity between the active site of an enzyme and the transition state of a reaction is one of the tenets of enzyme catalysis. This report illustrates the principles of enzyme catalysis (first proposed by Pauling and Jencks) through a well-defined model system that has been fully characterized crystallographically, computationally and kinetically. Catalysis of the bowl-to-bowl inversion processes that pertain to corannulene is achieved by combining ground-state destabilization and transition-state stabilization within the cavity of an extended tetracationic cyclophane. This synthetic receptor fulfils a role reminiscent of a catalytic antibody by stabilizing the planar transition state for the bowl-to-bowl inversion of (ethyl)corannulene (which accelerates this process by a factor of ten at room temperature) by an induced-fit mechanism first formulated by Koshland.

Original languageEnglish (US)
Pages (from-to)222-228
Number of pages7
JournalNature chemistry
Volume6
Issue number3
DOIs
StatePublished - Mar 2014

ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)

Fingerprint Dive into the research topics of 'Induced-fit catalysis of corannulene bowl-to-bowl inversion'. Together they form a unique fingerprint.

Cite this