title: A facile synthesis of α-N-ribosyl-asparagine and α-N-ribosyl-glutamine building blocks.
abstract: 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.
authors.affiliation: Dipartimento di Chimica, Universita' degli Studi di Milano, Via Golgi 19, 20133 Milano, Italy.
authors.forename: Gaetano
authors.initials: G
authors.lastname: Speciale
authors.forename: Anna
authors.initials: A
authors.lastname: Bernardi
authors.forename: Filippo
authors.initials: F
authors.lastname: Nisic
mesh_terms: D000244:Adenosine Diphosphate / Q000737:chemistry / Q000378:metabolism; D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D001216:Asparagine / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D060326:Chemistry Techniques, Synthetic; D005973:Glutamine / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D006031:Glycosylation; D011499:Protein Processing, Post-Translational
chemical_list: D000596:Amino Acids; D005973:Glutamine; D000244:Adenosine Diphosphate; D001216:Asparagine