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Specificity and Stereoselectivity of Cryptic Sulfotransferases

2025/02/05 by Sabina J. Maurer, Monica E. McCallum · 1 voice
Chemistry · Biochemistry, Genetics and Molecular Biology · #Mass Spectrometry Techniques and Applications #Amino Acid Enzymes and Metabolism #Analytical chemistry methods development

paper · doi:10.26434/chemrxiv-2025-gkxn3

Abstract

Sulfotransferases (STs) are ubiquitous enzymes found in all living organisms. These enzymes convert amines to sulfamates, and alcohols to sulfates, on a wide variety of biologically relevant molecules. Herein, we describe the characterization of a new subclass of ST that has been shown to facilitate the biosynthesis of azabicyclo[3.1.0] hexane (ABCH) natural products. We find that ST enzymes Fic28, Vzb21, and Azi31, enable stereoselective sulfation reactions on a variety of natural and unnatural amino alcohol substrates. We also demonstrate the chemoenzymatic conversion of these amino alcohols into chiral NH-aziridines. This reactivity accesses previously untapped substrates for sulfotransferases, with potential use in biocatalysis, resolution of racemic amino alcohols, and aziridination.

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