TY  - JOUR
AU  - Speciale, G
AU  - Bernardi, A
AU  - Nisic, F
Y2  - 2020/12/21
Y1  - 2013/07/24
SN  - 1420-3049
UR  - http://hdl.handle.net/11343/256895
AB  - 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.
LA  - eng
PB  - MDPI AG
T1  - A facile synthesis of α-N-ribosyl-asparagine and α-N-ribosyl-glutamine building blocks.
DO  - 10.3390/molecules18088779
IS  - Molecules
VL  - 18
IS  - 8
SP  - 8779-8785
L1  - /bitstream/handle/11343/256895/PMC6270248.pdf?sequence=1&isAllowed=y
ER  -