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A Facile Synthesis of α-N-Ribosyl-Asparagine and α-N-Ribosyl-Glutamine Building Blocks
Universita' degli Studi di Milano, Dipartimento di Chimica, via Golgi 19, 20133 Milano, Italy
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Received: 2 July 2013; in revised form: 16 July 2013 / Accepted: 19 July 2013 / Published: 24 July 2013
(This article belongs to the Special Issue ECSOC-16
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.
Keywords: ADP-ribosylation; glycoconjugates; ribofuranosyl aminoacids; Staudinger ligation; stereoselective synthesis
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MDPI and ACS Style
Speciale, G.; Bernardi, A.; Nisic, F. A Facile Synthesis of α-N-Ribosyl-Asparagine and α-N-Ribosyl-Glutamine Building Blocks. Molecules 2013, 18, 8779-8785.
Speciale G, Bernardi A, Nisic F. A Facile Synthesis of α-N-Ribosyl-Asparagine and α-N-Ribosyl-Glutamine Building Blocks. Molecules. 2013; 18(8):8779-8785.
Speciale, Gaetano; Bernardi, Anna; Nisic, Filippo. 2013. "A Facile Synthesis of α-N-Ribosyl-Asparagine and α-N-Ribosyl-Glutamine Building Blocks." Molecules 18, no. 8: 8779-8785.