Highly efficient syntheses of hyaluronic acid oligosaccharides

ORGN 410

Xiaowei Lu, xiaowei.lu@utoledo.edu1, Lijun Huang2, Bin Sun, bin.sun@utoledo.edu2, and Xuefei Huang, xuefei.huang@utoledo.edu2. (1) Department of Chemistry, University of Toledo, Toledo, OH 43606, (2) Department of Chemistry, The University of Toledo, 2801 w. Bancroft St, MS602, Toledo, OH 43606
Highly efficient syntheses of hyaluronic acid oligosaccharide have been accomplished through the pre-activation based iterative one-pot strategy. A series of oligosaccharides ranging from di- to deca-saccharides were rapidly assembled using only near stoichiometric amounts of the building blocks without aglycon adjustment or purifications of intermediate oligosaccharides. Deprotection and oxidation protocols were developed for protective group removal and oxidation-state adjustment. The availability of such structurally well defined synthetic hyaluronic acid oligosaccharides will greatly facilitate the establishment of detailed structure-function relationships.