Probing the reaction mechanism of aristolochene synthase with 12,13-difluorofarnesyl diphosphate

Fanglei Yu; David J Miller; Rudolf K Allemann

doi:10.1039/b709562g

Probing the reaction mechanism of aristolochene synthase with 12,13-difluorofarnesyl diphosphate

Chem Commun (Camb). 2007 Oct 28:(40):4155-7. doi: 10.1039/b709562g. Epub 2007 Aug 6.

Authors

Fanglei Yu¹, David J Miller, Rudolf K Allemann

Affiliation

¹ School of Chemistry, Cardiff University, Main Building, Park Place, Cardiff, UK CF10 3AT.

PMID: 17925960
DOI: 10.1039/b709562g

Abstract

12,13-Difluorofarnesyl diphosphate, prepared using Suzuki-Miyaura chemistry, is a potent inhibitor of aristolochene synthase (AS), indicating that the initial cyclisation during AS catalysis generates germacryl cation in a concerted reaction.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Catalysis
Diphosphates / chemistry*
Diphosphates / metabolism*
Isomerases / metabolism*
Molecular Structure
Polyisoprenyl Phosphates / chemistry
Polyisoprenyl Phosphates / metabolism
Sesquiterpenes / chemistry
Sesquiterpenes / metabolism

Substances

12,13-difluorofarnesyl diphosphate
Diphosphates
Polyisoprenyl Phosphates
Sesquiterpenes
Isomerases
aristolochene synthase