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Solid‐Phase Synthesis of 5′‐ O ‐[ N ‐(Acyl)sulfamoyl]adenosine Derivatives
Author(s) -
Redwan Itedale Namro,
Ingemyr Hanna Jacobson,
Ljungdahl Thomas,
Lawson Christopher P.,
Grøtli Morten
Publication year - 2012
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201200329
Subject(s) - chemistry , solid phase synthesis , amide , enzyme , stereochemistry , adenosine , combinatorial chemistry , polystyrene , organic chemistry , peptide , biochemistry , polymer
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.