Systematic synthesis of bisected N-glycans and unique recognitions by glycan-binding proteins,Chemical Science

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Systematic synthesis of bisected N-glycans and unique recognitions by glycan-binding proteins
Chemical Science ( IF 7.6 ) Pub Date : 2022-06-09 , DOI: 10.1039/d1sc05435j
Xuefeng Cao ₁ , Shuaishuai Wang ₁ , Madhusudhan Reddy Gadi ₁ , Ding Liu ₁ , Peng G Wang ₁ , Xiu-Feng Wan _{2,

3,

4,

5} , Jian Zhang ₆ , Xi Chen ₇ , Lauren E Pepi ₈ , Parastoo Azadi ₈ , Lei Li ₁

Affiliation

Bisected N-glycans represent a unique class of protein N-glycans that play critical roles in many biological processes. Herein, we describe the systematic synthesis of these structures. A bisected N-glycan hexasaccharide was chemically assembled with two orthogonal protecting groups attached at the C2 of the branching mannose residues, followed by sequential installation of GlcNAc and LacNAc building blocks to afford two asymmetric bisecting “cores”. Subsequent enzymatic modular extension of the “cores” yielded a comprehensive library of biantennary N-glycans containing the bisecting GlcNAc and presenting 6 common glycan determinants in a combinatorial fashion. These bisected N-glycans and their non-bisected counterparts were used to construct a distinctive glycan microarray to study their recognition by a wide variety of glycan-binding proteins (GBPs), including plant lectins, animal lectins, and influenza A virus hemagglutinins. Significantly, the bisecting GlcNAc could bestow (PHA-L, rDCIR2), enhance (PHA-E), or abolish (ConA, GNL, anti-CD15s antibody, etc.) N-glycan recognition of specific GBPs, and is tolerated by many others. In summary, synthesized compounds and the unique glycan microarray provide ideal standards and tools for glycoanalysis and functional glycomic studies. The microarray data provide new information regarding the fine details of N-glycan recognition by GBPs, and in turn improve their applications.

中文翻译：

二等分 N-聚糖的系统合成和聚糖结合蛋白的独特识别

二等分N-聚糖代表一类独特的蛋白质N-聚糖，在许多生物过程中起着关键作用。在此，我们描述了这些结构的系统合成。一分为二的N-聚糖六糖与连接在分支甘露糖残基 C2 处的两个正交保护基团进行化学组装，然后依次安装 GlcNAc 和 LacNAc 构建块以提供两个不对称的二等分“核心”。“核心”的后续酶促模块化延伸产生了一个全面的双触角N-聚糖库，其中包含平分的 GlcNAc 并以组合方式呈现 6 种常见的聚糖决定簇。这些平分N-聚糖及其未对分的对应物用于构建独特的聚糖微阵列，以研究它们被多种聚糖结合蛋白 (GBP) 识别，包括植物凝集素、动物凝集素和甲型流感病毒血凝素。值得注意的是，二等分 GlcNAc 可以赋予（PHA-L、rDCIR2）、增强（PHA-E）或消除（ConA、GNL、抗 CD15s 抗体等）特定 GBP 的 N-聚糖识别，并且被许多人耐受其他。总之，合成的化合物和独特的聚糖微阵列为糖分析和功能性糖组学研究提供了理想的标准和工具。微阵列数据提供了有关 GBP 识别N聚糖的细节的新信息，进而改进了它们的应用。

更新日期：2022-06-09

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