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Full Paper
Solid-Phase Synthesis of 5′-O-[N-(Acyl)sulfamoyl]adenosine Derivatives
Article first published online: 16 MAY 2012
DOI: 10.1002/ejoc.201200329
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Redwan, I. N., Ingemyr, H. J., Ljungdahl, T., Lawson, C. P. and Grøtli, M. (2012), Solid-Phase Synthesis of 5′-O-[N-(Acyl)sulfamoyl]adenosine Derivatives. Eur. J. Org. Chem., 2012: 3665–3669. doi: 10.1002/ejoc.201200329
Publication History
- Issue published online: 20 JUN 2012
- Article first published online: 16 MAY 2012
- Manuscript Received: 27 MAR 2012
Funded by
- Swedish Research Council. Grant Number: 62120083533
- Olle Engkvist Byggmästare Foundation
- Department of Chemistry and Molecular Biology, University of Gothenburg
Keywords:
- Medicinal chemistry;
- Synthetic methods;
- Solid-phase synthesis;
- Enzymes;
- Nucleosides
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.