Department of Chemistry and Chemical Biology, ‡Department of Biology, and §Departments of Chemical and Biological Engineering and Biomedical Engineering, Center for Biotechnology and Interdisciplinary Studies, Rensselaer Polytechnic Institute , Troy, New York 12180, United States.
Org Lett. 2014 Apr 18;16(8):2240-3. doi: 10.1021/ol500738g. Epub 2014 Apr 4.
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.
本文报道了通过酶促反应合成带有氟标签的肝素四糖（1）和六糖（2）。氟叔丁基碳酸酯（(F)Boc）标签不会干扰酶对延伸和特定硫酸化的识别，并且可以通过标准氟固相萃取（FSPE）进行快速纯化。基于带有氟标签的二糖作为受体，利用氟化学技术成功合成了一系列部分 N-硫酸化、6-O-硫酸化的肝素硫酸寡糖。
