Leiden Institute of Chemistry, Leiden University, P.O. Box 9502, 2300 RA Leiden, The Netherlands.
Org Lett. 2013 May 3;15(9):2306-9. doi: 10.1021/ol400929c. Epub 2013 Apr 24.
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.
研究了呋喃核糖基 N-苯三氟乙酰亚胺酯对天冬酰胺和谷氨酰胺的酰胺侧链的糖基化性质。找到了促进几乎完全形成α-构型 N-糖苷的条件。该策略可用于合成适合制备 ADP-核糖基化肽的 Fmoc-氨基酸。此外，用这些供体对丝氨酸进行核糖基化被证明是完全α-选择性的，并且首次合成了天然多 ADP-核糖基化位点的α-核糖基谷氨酸和天冬氨酸。
