Metal-Catalyzed Site-Selective Monoacylation of Diols in Aqueous Media

Yuyang Li; Ronald Kluger

doi:10.1055/s-0037-1611907

Synthesis, Table of Contents

Synthesis 2019; 51(20): 3784-3791
DOI: 10.1055/s-0037-1611907

short review

Metal-Catalyzed Site-Selective Monoacylation of Diols in Aqueous Media

Yuyang Li

,

Ronald Kluger∗

Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, ON, M5S 3H6, Canada

› Author Affiliations

Abstract

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Abstract

Site-selective reactions of water-soluble biomolecules are being developed to produce efficient conversions in water and water/solvent mixtures. This review focuses on the use of designs based on bis-bidentate chelation of large metal ions by diols to be acylated by a co-chelated water-stable reagent. Topics discussed include: 1. The preparation and properties of water-stable acyl phosphate monoesters and their reactions with diol-chelated metal ions. 2. Site-selective monoaminoacylation of 3′-terminal diols of RNA and their applications in protein engineering. 3. Site-selective monoacylation of sugars with acyl phosphate monoesters associated with metal ions, including lanthanum and lead. The combination of metal ion, 1,2-diol, and acyl phosphate monoester produces site-selective reactions in aqueous media that can produce a general approach to site-selective mono-(amino)acylation in RNA and carbohydrates.

1 Introduction

2 Synthetic Aminoacylation of tRNA

3 Activated Amino Acids in Water

4 Metal Ions and Their Effects on the Reactivity of Acyl Phosphate Monoesters

5 The Challenge of Site-Selective Acylation of Carbohydrates in Water

6 Conclusions and Prospects

Key words

site-selective - diol - acylation - aqueous - acyl phosphate monoesters - metal ions - chelation

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