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Molecules 2013, 18(8), 8779-8785; doi:10.3390/molecules18088779
Article

A Facile Synthesis of α-N-Ribosyl-Asparagine and α-N-Ribosyl-Glutamine Building Blocks

,
 and *
Universita' degli Studi di Milano, Dipartimento di Chimica, via Golgi 19, 20133 Milano, Italy
* Author to whom correspondence should be addressed.
Received: 2 July 2013 / Revised: 16 July 2013 / Accepted: 19 July 2013 / Published: 24 July 2013
(This article belongs to the Special Issue ECSOC-16)
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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 ADP-ribosylation; glycoconjugates; ribofuranosyl aminoacids; Staudinger ligation; stereoselective synthesis
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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.

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