CU(II) Catalyzed Hydrolysis of an Unactivated Ester Based on Reversible Conjugate Addition

Abstract

Summary: Copper (II) catalysis provides a 16,000-fold acceleration in the hydrolysis of methyl acrylate when a removable vicinal diamine ligand is used to increase the stability of the required copper chelate. The early work of Kroll, Bender, and Westheimer on metal ion-promoted hydrolyses of alpha-amino acid esters and amides has provided the impetus for numerous studies of metal ion promoted and catalyzed ester hydrolysis. Enzyme models of metalloesterase activity possess both the ester and the metal ligand covalently and irreversibly connected; cyclodextrin and micellar systems have served as noncovalent enzyme mimics. Despite the early successes using methyl esters of alpha-amino acids, little work has been directed toward the hydrolysis of unactivated substrates; Cobalt (III) catalysis of methyl acetate hydrolysis described by Chin stands as a notable exception. Organic chemistry, Metalloenzymes, Ethylenediamine, Chelation, Metals, Nonmetals.

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Document Details

Document Type
Technical Report
Publication Date
May 01, 1990
Accession Number
ADA221344

Entities

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  • Anthony W. Czarnik
  • Brook F. Duerr

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  • Ohio State University

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