1461715-91-2Relevant academic research and scientific papers
A facile synthesis of α-N-ribosyl-asparagine and α-N-ribosyl- glutamine building blocks
Speciale, Gaetano,Bernardi, Anna,Nisic, Filippo
, p. 8779 - 8785 (2013/09/23)
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 α-N-ribosyl- asparagine (α-N-ribosyl-Asn) and α-N-ribosyl-glutamine (α-Nribosyl-Gln) building blocks starting from 5-tert-butyldiphenylsilyl- β-D-ribofuranosyl azide. The N-glycosyl aminoacids are produced in good yields as pure α-anomers, suitably protected for peptide synthesis.
