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The mechanism of polyleucine catalysed asymmetric epoxidation

2004/01/01 by David R. Kelly, Stanley M. Roberts · 2 citations
Biochemistry, Genetics and Molecular Biology · Chemistry · #Chemical Synthesis and Analysis #Chemical Synthesis and Reactions #Synthetic Organic Chemistry Methods

paper · doi:10.1039/b404390c

openalex publication_date 2004/01/01 · openalex created_date 2025/10/10 · openalex updated_date 2026/01/13

Abstract

Catalysis in the Julia-Colonna epoxidation of alpha,beta-unsaturated ketones is due to binding of the hydroperoxide enolate intermediate by the three N-terminal amidic N-H groups of alpha-helical poly-leucine; the N-terminal pair forms an oxy-anion hole, whilst the third aids displacement of hydroxide.

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