Synthesis of Man5 and Man7 oligomannoses

CARB 94

Xuefei Huang, xuefei.huang@utoledo.edu and Nardos H Teumelsan, teumelsan@yahoo.com. Department of Chemistry, The University of Toledo, 2801 W Bancroft st, Toledo, OH 43606
Human antibody 2G12 neutralizes a broad range of HIV-1 isolates. It is one of the few broadly neutralizing monoclonal antibodies directed against HIV-1. Among other high mannoses, Man5 and Man7 oligomannoses have been found to have reactivity with antibody 2G12(1). Therefore, understanding of the 2G12-oligomannose interaction can be applied to carbohydrate based immunogen design. We plan to synthesis high mannoses, Man5 and Man7, via reactivity independent one-pot method (2). We have prepared three building blocks that are going to be used as donors and acceptors for the assembly of Man5 and Man7 oligomannoses. Optimization of reaction conditions in terms of acquiring better selectivity and yield has been explored and one-pot synthesis of these compounds will be discussed.