15 マイクロ経路内および固相上での効率的グリコシル化反応の開発を基盤としたN-結合型糖タンパク質糖鎖のライブラリー指向型合成研究(口頭発表の部)

概要

論文の詳細を見る
In this conference, we report our efforts on the "library-directed" solid-phase synthesis of N-linked glycans, for the first step toward investigating their biological functions. We have efficiently prepared the Manβ (1-4) GlcNTroc fragment C by developing the new dual Lewis acid/cation trap reagent, TMSB(C_6F_5)_4. On the other hand, a highly α-selective sialylation of sialic acid N-phenyltrifluoroacetimidate was achieved by introducing the C-5 N-phthalylimide or the azide groups on the donor; the "fixed dipole moment effects" of these C-5 functional groups was proposed to explain the high reactivity and excellent α-selectivity. The microfluidic system was then applied to the present α-sialylation, which is amenable to large-scale synthesis of the Neu5Acα(2-6)Gal fragment D. The mono- and disaccharide fragments A-D thus prepared were efficiently glycosylated on the JandaJel^<TM> resin, by the use of the N-phenyltrifluoroacetimidate as the leaving group. In order to overcome the retarded reactivity on the solid-supports, especially for the glycosylation on the elongated sugar chain, the "reagent concentration effects" by using the fluorous solvent was successfully applied to the efficient glycosylation on the solid supports. A large-scale reductive cleavage of the benzylidene acetal group under the microfluidic conditions was also developed during the current N-glycan synthesis. The orchestration of these methods led to the efficient synthesis of the complex-type N-glycans, i.e., the core pentasaccharide as well as the octasaccharide, which contains the non-reducing end sialic acid, for the first time.
天然有機化合物討論会の論文
2008-09-01

15 マイクロ経路内および固相上での効率的グリコシル化反応の開発を基盤としたN-結合型糖タンパク質糖鎖のライブラリー指向型合成研究(口頭発表の部)

スポンサーリンク

概要

著者

関連論文

スポンサーリンク