Chao Cai, Demetria M Dickinson, Lingyun Li, Sayaka Masuko, Matt Suflita, Victor Schultz, Shawn D Nelson, Ujjwal Bhaskar, Jian Liu, Robert J Linhardt
The chemoenzymatic synthesis of heparan sulfate tetrasaccharide (1) and hexasaccharide (2) with a fluorous tag attached at the reducing end is reported. The fluorous tert-butyl dicarbonate ((F)Boc) tag did not interfere with enzymatic recognition for both elongation and specific sulfation, and flash purification was performed by standard fluorous solid-phase extraction (FSPE). Based on an (F)Boc attached disaccharide as acceptor, a series of partial N-sulfated, 6-O-sulfated heparan sulfate oligosaccharides were successfully synthesized employing fluorous techniques...
April 18, 2014: Organic Letters