Document Type

Article

Publication Date

2012

Journal or Book Title

Organic Letters

Volume

14

Issue

23

First Page

5828

Last Page

5831

DOI

10.1021/ol3026022

Abstract

Class II diterpene cyclases catalyze bicyclization of geranylgeranyl diphosphate. While this reaction typically is terminated via methyl deprotonation to yield copalyl diphosphate, in rare cases hydroxylated bicycles are produced instead. Abietadiene synthase is a bifunctional diterpene cyclase that usually produces a copalyl diphosphate intermediate. Here it is shown that substitution of aspartate for a conserved histidine in the class II active site of abietadiene synthase leads to selective production of 8α-hydroxy-CPP instead, demonstrating striking plasticity.

Comments

Reprinted (adapted) with permission from Organic Letters 14 (2012): 5828, doi:10.1021/ol3026022. Copyright 2012 American Chemical Society.

Rights

One-time permission is granted only for the use specified in your request. No additional uses are granted (such as derivative works or other editions). For any other uses, please submit a new request.

Copyright Owner

American Chemical Society

Language

en

File Format

application/pdf

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