Fluorous-Assisted Chemoenzymatic Synthesis of Heparan Sulfate Oligosaccharides

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• 作者：Chao Cai ; Demetria M. Dickinson ; Lingyun Li ; Sayaka Masuko ; Matt Suflita ; Victor Schultz ; Shawn D. Nelson ; Ujjwal Bhaskar ; Jian Liu ; Robert J. Linhardt
• 刊名：Organic Letters
• 出版年：2014
• 出版时间：April 18, 2014
• 年：2014
• 卷：16
• 期：8
• 页码：2240-2243
• 全文大小：351K
• 年卷期：v.16,no.8(April 18, 2014)
• ISSN：1523-7052

文摘

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.