A facile synthesis of α-N-ribosyl-asparagine and α-N-ribosyl-glutamine building blocks.
AuthorSpeciale, G; Bernardi, A; Nisic, F
University of Melbourne Author/sSPECIALE, GAETANO
AffiliationSchool of Chemistry
Document TypeJournal Article
CitationsSpeciale, G., Bernardi, A. & Nisic, F. (2013). A facile synthesis of α-N-ribosyl-asparagine and α-N-ribosyl-glutamine building blocks.. Molecules, 18 (8), pp.8779-8785. https://doi.org/10.3390/molecules18088779.
Access StatusOpen Access
Open Access at PMChttp://www.ncbi.nlm.nih.gov/pmc/articles/PMC6270248
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-N-ribosyl-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.
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