August 31, 2018
Keio University
Associate Professor Daisuke Takahashi, Professor Kazunobu Toshima, and their research group at the Department of Applied Chemistry, Faculty of Science and Technology, Keio University, have successfully developed a new organic chemistry method to synthesize β-L-rhamnopyranosides (hereafter β-rhamnosides) with complete stereoselectivity using organoboron compounds. Among "glycans," which are molecules in which monosaccharides are linked in a chain, the efficient and stereoselective synthesis of β-rhamnosides has been a significant challenge.
β-rhamnosides are found as antigens in various pathogenic bacteria, including *Streptococcus pneumoniae* and *Escherichia coli*, and are therefore highly anticipated for application in vaccines. However, β-rhamnosides extracted from pathogenic bacteria are structurally heterogeneous and obtained as a mixture with other molecules, which created the risk of including toxic components derived from the pathogens. In contrast, applying the organic chemistry method developed in this study enables the efficient synthesis of uniform glycan antigens that do not contain toxic components, which is expected to lead to the development and advancement of safer vaccines.
The results of this research were published in the online edition of the German Chemical Society's journal, *Angewandte Chemie International Edition*, on August 11, 2018.
Please see below for the full press release.