Fluorous-Assisted Chemoenzymatic Synthesis of HeparanSulfate Oligosaccharides

摘要

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 (^FBoc) 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 ^FBoc attached disaccharide as acceptor, a series of partial N-sulfated, 6-O-sulfated heparan sulfate oligosaccharides were successfully synthesized employing fluorous techniques.