Enzyme-Catalyzed Irreversible Acyl Transfer

Kurt Faber; Sergio Riva

doi:10.1055/s-1992-26255

Synthesis 1992; 1992(10): 895-910
DOI: 10.1055/s-1992-26255

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Enzyme-Catalyzed Irreversible Acyl Transfer

Kurt Faber^* , Sergio Riva

^*Institute of Organic Chemistry, Graz University of Technology, Stremayrgasse 16, A-8010 Graz, Austria

Abstract

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This paper reviews the present state of enzyme-catalyzed acyltransfer reactions, which represent a highly useful method for the transformation of alcoholic and amino functional groups in a chemo-, regio- and enantioselective fashion. 1. Introduction 2. Acyl-Transfer Techniques 2.1. Quasi-Irreversible Acyl Donors 2.2. Irreversible Acyl Donors 2.3. Other Acyl Donors 3. Synthetic Applications 3.1. Separation of E/Z-Stereoisomers 3.2. Asymmetrization of Prochiral or meso-Diols 3.3. Enzymatic Resolution of Primary and Secondary Alcohols 3.4. Enzymatic Resolution of Labile Hydroxy Compounds 3.5. Regioselective Protection of Polyhydroxy Compounds 3.5.1. Enzymatic Acylation of Carbohydrates 3.5.2. Enzymatic Acylation of Natural Glycosides 3.5.3. Regio- and Chemoselective Acylation of Alkaloids 3.5.4. Regioselective Acylation of Polyhydroxy Steroids 4. Preparative Procedures 5. Final Remarks

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