Aromatic Claisen Rearrangements of O-prenylated Tyrosine and Model Prenyl Aryl Ethers: Computational Study of the Role of Water on Acceleration of Claisen Rearrangements

Overview

Journal European J Org Chem

Specialty Biochemistry

Date 2013 Dec 31

PMID 24376368

Citations 5

Authors

Silvia Osuna

Seonah Kim

Guillaume Bollot

K N Houk

Affiliations

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Abstract

LynF, an enzyme from the TruF family, O-prenylates tyrosines in proteins; subsequent Claisen rearrangements give C-prenylated tyrosine products. These reactions in tyrosines and model phenolic systems have been explored with DFT and SCS-MP2 calculations. Various benchmarks have been computed (CBS-QB3, MP2, SCS-MP2) to examine the accuracy of commonly used density functionals, such as B3LYP and M06-2X. Solvent effects from water were considered using implicit and explicit models. Studies of the -C-prenylation and Claisen rearrangement of tyrosine, and the Claisen rearrangement of α,α-dimethylallyl (prenyl) coumaryl ether establish the energetics of these reactions in the gas phase and in aqueous solution.

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