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Investigation, optimization and synthesis of sulfamoyloxy-linked aminoacyl-AMP analogues

Journal article
Authors Itedale Namro Redwan
Thomas Ljungdahl
Morten Grøtli
Published in Tetrahedron
Volume 68
Pages 1507-1514
ISSN 00404020
Publication year 2012
Published at Department of Chemistry and Molecular Biology
Pages 1507-1514
Language en
Links doi.org/10.1016/j.tet.2011.12.011
Keywords Amide bond formation, Aminoacyl-tRNA synthetases, Catalytic hydrogenation, Protection group chemistry, Sulfamoyloxy-linked aminoacyl-AMP analogues
Subject categories Chemistry

Abstract

Aminoacyl-tRNA synthetases (aaRSs) constitute a family of enzymes that transfer amino acids to their corresponding tRNA molecules to form aminoacyl-tRNAs and have been validated as potential drug targets. Sulfamoyloxy-linked aminoacyl-AMP analogues are potent inhibitors of aaRSs. In this article, we report the synthesis of several new sulfamoyl analogues of aa-AMP that up to now have been difficult or even impossible to prepare with current synthetic strategies. The developed synthetic strategy relies on performing the synthesis under neutral conditions followed by global deprotection using catalytic hydrogenation affording the desired 5′-O-(N-aminoacyl)sulfamoyladenosine compounds. © 2011 Elsevier Ltd. All rights reserved.

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