1220340-28-2Relevant academic research and scientific papers
A facile synthesis of α-N-ribosyl-asparagine and α-N-ribosyl- glutamine building blocks
Speciale, Gaetano,Bernardi, Anna,Nisic, Filippo
, p. 8779 - 8785 (2013/09/23)
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-Nribosyl-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.
Synthesis of mono-ADP-ribosylated oligopeptides using ribosylated amino acid building blocks
Van Der Heden Van Noort, Gerbrand J.,Van Der Horst, Maarten G.,Overkleeft, Herman S.,Van Der Marel, Gijsbert A.,Filippov, Dmitri V.
supporting information; experimental part, p. 5236 - 5240 (2010/06/19)
Adenosine diphosphate ribosylation (ADP-ribosylation) is a widely occurring post-translational modification of proteins at nucleophilic side chains of amino acid residues, such as asparagine, glutamic acid, and arginine. Elucidation of the biological role of ADP-ribosylation events would benefit from the availability of well-defined ADP-ribosylated peptides. Main issues in the construction of synthetic ADP-ribosylated peptides involve the availability of protected ribosylated amino acids suitable for peptide synthesis, development of a protective group strategy for peptide fragments compatible with the integrity of the adenosine diphosphate moiety, and an efficient procedure for pyrophosphate formation. In this paper we present a first approach to the chemical synthesis of ADP-ribosylated peptides in solution and on solid support. We describe an efficient synthesis of suitably protected ribosylated asparagine and glutamine building blocks suitable for Fmoc-based peptide synthesis. We further demonstrate a successful application of these ribosylated amino acids in the assembly of three fully synthetic ADP-ribosylated peptides by solution and solid phase approaches.
