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首页> 外文期刊>Chemical science >Making the longest sugars: a chemical synthesis of heparin-related [4]n oligosaccharides from 16-mer to 40-mer
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Making the longest sugars: a chemical synthesis of heparin-related [4]n oligosaccharides from 16-mer to 40-mer

机译:制作最长糖:肝素相关的[4] n 寡糖从16-mer到40-mer的化学合成

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The chemical synthesis of long oligosaccharides remains a major challenge. In particular, the synthesis of glycosaminoglycan (GAG) oligosaccharides belonging to the heparin and heparan sulfate (H/HS) family has been a high profile target, particularly with respect to the longer heparanome. Herein we describe a synthesis of the longest heparin-related oligosaccharide to date and concurrently provide an entry to the longest synthetic oligosaccharides of any type yet reported. Specifically, the iterative construction of a series of [4]n-mer heparin-backbone oligosaccharides ranging from 16-mer through to the 40-mer in length is described. This demonstrates for the first time the viability of generating long sequence heparanoids by chemical synthesis, via practical solution-phase synthesis. Pure-Shift HSQC NMR provides a dramatic improvement in anomeric signal resolution, allowing full resolution of all 12 anomeric protons and extrapolation to support anomeric integrity of the longer species. A chemically pure 6-O-desfulfated GlcNS-IdoAS icosasaccharide (20-mer) represents the longest pure synthetic heparin-like oligosaccharide.
机译:长寡糖的化学合成仍然是主要挑战。特别地,属于肝素和硫酸乙酰肝素(H / HS)家族的糖胺聚糖(GAG)寡糖的合成已成为备受关注的目标,特别是对于更长的肝素瘤。本文中,我们描述了迄今为止最长的肝素相关寡糖的合成,同时提供了迄今为止尚未报道的任何类型的最长合成寡糖的条目。具体而言,迭代构建一系列的[4] n -mer肝素-骨干寡糖,其范围从16-mer到40-描述了长度的mer。这首次证明了通过实用的溶液相合成方法 通过化学合成方法产生长序列类花生四烯酸的可行性。 Pure-Shift HSQC NMR大大改善了异头物信号的分辨率,允许全部12个异头物质子的全分辨率和外推法,以支持更长物种的异头物完整性。化学上纯净的6- O -去饱和的GlcNS-IdoAS寡糖(20-mer)代表最长的纯合成肝素样寡糖。

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