|
|||||
|
|
A novel method for the formation of N-glycosides using hydroxamate |
|
| Authors: | Jun Nakano Tsuyoshi Ichiyanagi Hiromichi OhtaYukishige Ito |
| Institution: | a RIKEN (The Institute of Physical and Chemical Research), 2-1 Hirosawa, Wako-shi, Saitama 351-0198, Japan b Department of Chemistry, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama 223-0061, Japan c CREST, JST, Kawaguchi, Saitama 332-0012, Japan |
| Abstract: | Direct formation of Asn-linked carbohydrate by N-glycosylation has been difficult, because of the lack of nucleophilicity of carboxamide nitrogen. We report here the novel N-glycosylation using Asn hydroxamate as a glycosyl acceptor. Reaction with glycosyl fluoride or glycosyl trichloroacetimidate afforded N-glycoside and subsequent reduction with SmI2 gave Asn-linked glucose. Carbamate derived hydroxamates proved to have even enhanced reactivity to give N-glycosides in high yields. |
| Keywords: | N-glycoside asparagine hydroxamate |
| 本文献已被 ScienceDirect 等数据库收录！ | |