Solid-Phase Synthesis of 5 '-O- N-(Acyl)sulfamoyl adenosine Derivatives
Journal article, 2012
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.
siderophore
adenylate
transfer-rna synthetase
Synthetic methods
mycobacterium-tuberculosis
Nucleosides
pantothenate synthetase
Solid-phase synthesis
Enzymes
Medicinal chemistry
acid
antibiotics
inhibitors
biosynthesis
analogs
Author
Itedale Namro Redwan
University of Gothenburg
Hanna Jacobson Ingemyr
University of Gothenburg
Thomas Ljungdahl
Chalmers, Chemical and Biological Engineering, Physical Chemistry
Christopher Lawson
Chalmers, Chemical and Biological Engineering, Physical Chemistry
Morten Grötli
University of Gothenburg
European Journal of Organic Chemistry
1434-193X (ISSN) 10990690 (eISSN)
Vol. 2012 19 3665-3669Subject Categories
Pharmaceutical Chemistry
DOI
10.1002/ejoc.201200329