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Chemo-enzymatic Synthesis of N-glycans for Array Development and HIV Antibody Profiling
Published on: February 5, 2018
Synthesis of a sialic acid containing complex-type N-glycan on a solid support
Katsunori Tanaka1, Yohei Fujii, Hiroomi Tokimoto
1Department of Chemistry, Graduate School of Science, Osaka University, 1-1 Machikaneyama-cho, Toyonaka-shi, Osaka 560-0043, Japan.
Chemistry, an Asian Journal
|January 22, 2009
Summary
This study reports a novel solid-phase synthesis for N-linked glycans, achieving stereoselective beta-mannosylation and microfluidic alpha-sialylation. This method enables the first solid-phase synthesis of complex N-glycans containing sialic acid.
Area of Science:
- Carbohydrate Chemistry
- Glycobiology
- Organic Synthesis
Background:
- N-linked glycans are crucial biomolecules involved in various biological processes.
- Solid-phase synthesis offers advantages for complex carbohydrate assembly.
- Efficient methods for sialic acid incorporation are needed.
Purpose of the Study:
- To develop a novel solid-phase synthesis for complex N-linked glycans.
- To achieve stereoselective beta-mannosylation and microfluidic alpha-sialylation.
- To enable the first solid-phase synthesis of sialic acid-containing N-glycans.
Main Methods:
- Solid-phase synthesis utilizing JandaJel resin.
- Stereoselective beta-mannosylation reactions.
- Microfluidic alpha-sialylation techniques.
- Application of fluorous solvent effects for reagent concentration control.
Main Results:
- Successful stereoselective beta-mannosylation.
- Efficient microfluidic alpha-sialylation.
- Effective glycosylation of N-phenyltrifluoroacetimidate units.
- First synthesis of a sialic acid-containing complex-type N-glycan on a solid support.
Conclusions:
- A robust solid-phase synthesis for complex N-glycans has been established.
- The developed methods allow for precise control over glycosylation.
- This work provides a platform for synthesizing structurally defined sialylated N-glycans.
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