1430197-49-1Relevant articles and documents
Stereoselective ribosylation of amino acids
Kistemaker, Hans A. V.,Van Der Heden Van Noort, Gerbrand J.,Overkleeft, Herman S.,Van Der Marel, Gijsbert A.,Filippov, Dmitri V.
supporting information, p. 2306 - 2309 (2013/06/05)
The glycosylation properties of ribofuranosyl N-phenyltrifluoroacetimidates toward carboxamide side chains of asparagine and glutamine were investigated. Conditions were found that promote nearly exclusive formation of the α-anomerically configured N-glycosides. The strategy allows for the synthesis of Fmoc-amino acids suitably modified for the preparation of ADP-ribosylated peptides. Furthermore, ribosylation of serine with these donors proved to be completely α-selective, and for the first time, α-ribosylated glutamic and aspartic acid, the naturally occurring sites for poly-ADP-ribosylation, were synthesized.