Solid-Phase Synthesis of 5′-O-[N-(Acyl)sulfamoyl]adenosine Derivatives

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Abstract

The solid-phase synthesis of 5′-O-[N-(acyl)sulfamoyl]adenosine derivatives is described. The use of a Rink amide polystyrene solid support together with an appropriately protected ribo-purine starting material allowed for the development of a highly reliable and practical route for the solid-phase synthesis of 5′-O-[N-(acyl)sulfamoyl]adenosines. The developed procedure enables the efficient parallel synthesis of the target compounds in high yields. These compounds are non-hydrolysable isosteres of acyl-adenylates, which play an important role in a range of different metabolic pathways such as ribosomal and non-ribosomal peptide synthesis, fatty acid oxidation or enzyme regulation; some adenylate-forming enzymes are potential drug targets.

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