%0 Journal Article
%T A Facile Synthesis of ¦Á-N-Ribosyl-Asparagine and ¦Á-N-Ribosyl-Glutamine Building Blocks
%A Gaetano Speciale
%A Anna Bernardi
%A Filippo Nisic
%J Molecules
%D 2013
%I MDPI AG
%R 10.3390/molecules18088779
%X Adenosine diphosphate ribosylation (ADP-ribosylation) is a widely occurring post-translational modification of proteins at nucleophilic side chain of amino acid residues. Elucidation of ADP-ribosylation events would benefit greatly from the availability of well-defined ADP-ribosylated peptides and analogues thereof. In this paper we present a novel approach to the chemical synthesis of ribosylated amino acid building blocks using traceless Staudinger ligation. We describe an efficient and stereoselective synthesis of ¦Á- N-ribosyl-asparagine (¦Á- N-ribosyl-Asn) and ¦Á- N-ribosyl-glutamine (¦Á- N-ribosyl-Gln) building blocks starting from 5- tert-butyldiphenylsilyl-¦Â-d-ribofuranosyl azide. The N-glycosyl aminoacids are produced in good yields as pure ¦Á-anomers, suitably protected for peptide synthesis.
%K ADP-ribosylation
%K glycoconjugates
%K ribofuranosyl aminoacids
%K Staudinger ligation
%K stereoselective synthesis
%U http://www.mdpi.com/1420-3049/18/8/8779