Stereoselective Ribosylation of Amino Acids

作者：Kistemaker Hans A V; van Noort Gerbrand J van der Heden; Overkleeft Herman S; van der Marel Gij**ert A^*; Filippov Dmitri V

来源：Organic Letters, 2013, 15(9): 2306-2309.

DOI：10.1021/ol400929c

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 alpha-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 alpha-selective, and for the first time, alpha-ribosylated glutamic and aspartic acid, the naturally occurring sites for poly-ADP-ribosylation, were synthesized.

• 出版日期2013-5-3