1262335-48-7Relevant academic research and scientific papers
Convergent Synthesis of a Bisecting N-Acetylglucosamine (GlcNAc)-Containing N-Glycan
Manabe, Yoshiyuki,Shomura, Hiroki,Minamoto, Naoya,Nagasaki, Masahiro,Takakura, Yohei,Tanaka, Katsunori,Silipo, Alba,Molinaro, Antonio,Fukase, Koichi
, p. 1544 - 1551 (2018/05/30)
The chemical synthesis of a bisecting N-acetylglucosamine (GlcNAc)-containing N-glycan was achieved by a convergent synthetic route through [4+2] and [6+2] glycosylations. This synthetic route reduced the number of reaction steps, although the key glycosylations were challenging in terms of yields and selectivities owing to steric hindrance at the glycosylation site and a lack of neighboring group participation. The yields of these glycosylations were enhanced by stabilizing the oxocarbenium ion intermediate through ether coordination. Glycosyl donor protecting groups were explored in an effort to realize perfect α selectivity by manipulating remote participation. The simultaneous glycosylations of a tetrasaccharide with two disaccharides was investigated to efficiently construct a bisecting GlcNAc-containing N-glycan.
Synthesis of a sialic acid containing complex-type n-glycan on a solid support
Tanaka, Katsunori,Fujii, Yohei,Tokimoto, Hiroomi,Mori, Yasutaka,Tanaka, Shin-Ichi,Bao, Guang-Ming,Siwu, Eric R. O.,Nakayabu, Aiko,Fukase, Koichi
supporting information; experimental part, p. 574 - 580 (2010/04/23)
A new solid-phase synthesis of N-linked glycans featuring 1) highly ste-reoselective b-mannosylation and microfluidic a-sialylation and 2) efficient glycosylation of the N-phenyltrifluoroacetimidate units on JandaJel resin is reported. Reagent concentration effects by a fluorous solvent are effectively applied, and the use of these methods results in the first synthesis of a sialic acid containing complex-type N-glycan on a solid support.
