Efficient Convergent Synthesis of Bi-, Tri-, and Tetra-antennary Complex Type N-Glycans and Their HIV-1 Antigenicity
| Autor: | Hong-Yang Chuang, Li Hsu, Chi-Huey Wong, Chien-Tai Ren, Chih-Wei Lin, Tsung-I Tsai, Shiou-Ting Li, Sachin S. Shivatare, Chung-Yi Wu, Shih-Huang Chang |
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| Rok vydání: | 2013 |
| Předmět: |
AIDS Vaccines
chemistry.chemical_classification Glycan Antigenicity Glycosylation biology Chemistry Molecular Sequence Data Convergent synthesis HIV General Chemistry HIV Antibodies Biochemistry Catalysis Sialic acid carbohydrates (lipids) chemistry.chemical_compound Colloid and Surface Chemistry Polysaccharides Carbohydrate Conformation biology.protein Carbohydrate conformation HIV vaccine Glycoprotein |
| Zdroj: | Journal of the American Chemical Society. 135:15382-15391 |
| ISSN: | 1520-5126 0002-7863 |
| DOI: | 10.1021/ja409097c |
| Popis: | The structural diversity of glycoproteins often comes from post-translational glycosylation with heterogeneous N-glycans. Understanding the complexity of glycans related to various biochemical processes demands a well-defined synthetic sugar library. We report herein a unified convergent strategy for the rapid production of bi-, tri-, and tetra-antennary complex type N-glycans with and without terminal N-acetylneuraminic acid residues connected via the α-2,6 or α-2,3 linkages. Moreover, using sialyltransferases to install sialic acid can minimize synthetic steps through the use of shared intermediates to simplify the complicated procedures associated with conventional sialic acid chemistry. Furthermore, these synthetic complex oligosaccharides were compiled to create a glycan array for the profiling of HIV-1 broadly neutralizing antibodies PG9 and PG16 that were isolated from HIV infected donors. From the study of antibody PG16, we identified potential natural and unnatural glycan ligands, which may facilitate the design of carbohydrate-based immunogens and hasten the HIV vaccine development. |
| Databáze: | OpenAIRE |
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