1. Department of Chemistry, National Tsing Hua University, Hsinchu 300, Taiwan
2. Genomics Research Center,
3. Institute of Chemistry,
4. Chemical Biology and Molecular Biophysics Program, Taiwan International Graduate Program, Academia Sinica, Taipei 115, Taiwan

Correspondence to: Shang-Cheng Hung^1,2,3,4 Correspondence and requests for materials should be addressed to S.-C.H. (Email: hung@mx.nthu.edu.tw).

Abstract

Carbohydrates are involved in a wide range of biological processes^{1, 2, 3, 4}. These structurally diverse compounds are more complex than other biological polymers, and are often present as heterogeneous mixtures in nature. The chemical synthesis of carbohydrates is one way to obtain pure oligosaccharides, but it is hampered by difficulties associated with the regioselective protection of polyhydroxyls and challenges related to the stereoselective assembly of glycosidic linkages^{5, 6, 7, 8, 9, 10, 11, 12, 13, 14}. Here we describe a combinatorial, and highly-regioselective, method that can be used to protect individual hydroxy groups of a monosaccharide. This approach can be used to install an orthogonal protecting group pattern in a single reaction vessel (a 'one-pot' reaction), which removes the need to carry out the time-consuming isolation and purification of intermediates. Hundreds of building blocks have been efficiently prepared starting from d-glucose, and the iterative coupling of these building blocks enabled us to assemble -1,6-glucans and a library of oligosaccharides based on the influenza-virus-binding trisaccharide.

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