Regioselective one-pot protection of carbohydrates.
Carbohydrates are involved in a wide range of biological processes. 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. 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 beta-1,6-glucans and a library of oligosaccharides based on the influenza-virus-binding trisaccharide.
Wang
Cheng-Chung
CC
Department of Chemistry, National Tsing Hua University, Hsinchu 300, Taiwan.
Lee
Jinq-Chyi
JC
Luo
Shun-Yuan
SY
Kulkarni
Suvarn S
SS
Huang
Yu-Wen
YW
Lee
Chia-Chen
CC
Chang
Ken-Lien
KL
Hung
Shang-Cheng
SC
D000818:Animals; D001717:Birds / Q000821:virology; D002240:Carbohydrate Sequence; D002384:Catalysis; D006001:Glycoconjugates / Q000138:chemical synthesis* / Q000737:chemistry* / Q000378:metabolism; D006801:Humans; D053124:Influenza A Virus, H5N1 Subtype / Q000235:genetics / Q000378:metabolism; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry* / Q000378:metabolism; D011991:Receptors, Virus / Q000737:chemistry / Q000378:metabolism
D006001:Glycoconjugates; D009844:Oligosaccharides; D011991:Receptors, Virus