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

Molecules

Gaetano Speciale¹  Anna Bernardi¹ 

[1] Universita’ degli Studi di Milano, Dipartimento di Chimica, via Golgi 19, 20133 Milano, Italy;

关键词: ADP-ribosylation;    glycoconjugates;    ribofuranosyl aminoacids;    Staudinger ligation;    stereoselective synthesis;   

DOI  :  10.3390/molecules18088779

来源: mdpi

【 摘 要 】

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.

【 授权许可】

CC BY   
© 2013 by the authors; licensee MDPI, Basel, Switzerland.