5-azidopentyl-O-2-O-acetyl-4,6-O-benzylidine-β-D-mannopyranosyl-(1→4)-O-(3,6-di-Obenzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1→4)-O-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside | 1169693-83-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-azidopentyl-O-2-O-acetyl-4,6-O-benzylidine-β-D-mannopyranosyl-(1→4)-O-(3,6-di-Obenzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1→4)-O-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside
• 英文别名: 5-azidopentyl 2-O-acetyl-4,6-O-benzylidene-β-D-mannopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalamido-β-D-glucopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalamido-β-D-glucopyranoside
• CAS: 1169693-83-7
• 化学式: C₇₆H₇₇N₅O₁₉
• 分子量: 1364.47
• InChiKey: YEXAVCCHQGBDGR-IOERBKSESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.77
• 重原子数：
  100.0
• 可旋转键数：
  29.0
• 环数：
  13.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  280.81
• 氢给体数：
  1.0
• 氢受体数：
  20.0

反应信息

• 作为反应物：
  描述：

  5-azidopentyl-O-2-O-acetyl-4,6-O-benzylidine-β-D-mannopyranosyl-(1→4)-O-(3,6-di-Obenzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1→4)-O-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 、 在 二氯二茂铪 、 silver trifluoromethanesulfonate 作用下， 以 甲苯 为溶剂， 以50%的产率得到
  参考文献：
  名称：

  通过选择性酶促糖基化反应合成不对称的N-糖类作为通用核心底物，实现结构多样化。

  摘要：

  细胞表面的N-聚糖具有独特的特征，可被不同的聚糖结合蛋白（GBP）和病原体识别。人类中的大多数聚糖是不对称和异构的，但由于缺乏研究性，人们对其生物学功能的了解还不够。在这项工作中，我们开发了一种改进的N不对称策略-聚糖的组装和多样化，使用设计的通用核心底物进行化学制备，用于选择性酶促岩藻糖基化和唾液酸化。在微阵列中使用所得的26个在不同触角上带有唾液酸残基的明确定义的聚糖作为代表性应用，以分析禽流感病毒（H5N2）的血凝素（HA）的结合特异性。我们发现与Neu5Ac-Gal表位连接到不同分支的N-乙酰氨基葡萄糖（GlcNAc）有独特的结合亲和力，并且在结合不同分支上的末端半乳糖方面只有很小的作用。总体而言，微阵列分析显示了分支偏向和基于上下文的识别模式。

  DOI：

  10.1021/acschembio.0c00359
• 作为产物：
  描述：

  5-azidopentyl 2-O-acetyl-4,6-O-benzylidene-3-O-(2-naphthylmethyl)-β-D-mannopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalamido-β-D-glucopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalamido-β-D-glucopyranoside 在 2,3-二氯-5,6-二氰基-1,4-苯醌 、 水 、 碳酸氢钠 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以56%的产率得到5-azidopentyl-O-2-O-acetyl-4,6-O-benzylidine-β-D-mannopyranosyl-(1→4)-O-(3,6-di-Obenzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1→4)-O-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of a core trisaccharide building block for the assembly of N-glycan neoconjugates

  摘要：

  A short and high yielding synthesis of a core trisaccharide 1 as the key building block in the assembly of a library of N-glycan neoconjugates is presented. The beta-D-Manp-(1 -> 4)-D-GlcpNAc linkage was introduced by inversion of the C-2 position of a beta-glucoside. The glucosyl donor was efficiently synthesised following a recently published one-pot strategy. 2-Naphthylmethyl and benzylidene-acetal protection in the terminal mannose permitted selective liberation of main branching sites for subsequent glycosylation. A C5 azido linker attached to the anomeric position, which is stable throughout the synthesis, will allow for the posterior immobilisation of deprotected glycans on a microarray surface. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.02.028

文献信息

• Chemoenzymatic Synthesis of N-glycan Positional Isomers and Evidence for Branch Selective Binding by Monoclonal Antibodies and Human C-type Lectin Receptors
  作者：Begoña Echeverria、Sonia Serna、Silvia Achilli、Corinne Vivès、Julie Pham、Michel Thépaut、Cornelis H. Hokke、Franck Fieschi、Niels-Christian Reichardt

  DOI：10.1021/acschembio.8b00431

  日期：2018.8.17

  Here, we describe a strategy for the rapid preparation of pure positional isomers of complex N-glycans to complement an existing array comprising a larger number of N-glycans and smaller glycan structures. The expanded array was then employed to study context-dependent binding of structural glycan fragments by monoclonal antibodies and C-type lectins. A partial enzymatic elongation of semiprotected

  在这里，我们描述了一种快速制备复杂N-聚糖的纯位置异构体的策略，以补充包含大量N-聚糖和较小聚糖结构的现有阵列。然后将扩展的阵列用于研究单克隆抗体和C型凝集素对结构聚糖片段的背景依赖性结合。通过制备型HPLC将半保护核心结构的部分酶促延伸与位置异构体的保护基辅助分离相结合。该方法避免了繁琐的触角化学区分，被用于制备八种带有Galβ1,4GlcNAc（LN），GalNAcβ1,4GlcNAc（LDN）和GalNAcβ1,4[Fucα1,3] GlcNAc（LDNF）的双触角N-聚糖。 ）出现在一个或两个触角上的图案。三种抗Le抗体结合特异性的筛选针对曼氏沙门氏菌聚糖和先天免疫系统的三个C型凝集素受体（即DC-SIGN，DC-SIGNR和LSECtin）产生的X单克隆IgM抗体显示出令人惊讶的上下文相关的精细特异性，可识别聚糖基序。此外，我们观察到，通过测试的C型凝集素，一个单独的位置异构体比
• Efficient Convergent Synthesis of Bi-, Tri-, and Tetra-antennary Complex Type <i>N</i>-Glycans and Their HIV-1 Antigenicity
  作者：Sachin S. Shivatare、Shih-Huang Chang、Tsung-I Tsai、Chien-Tai Ren、Hong-Yang Chuang、Li Hsu、Chih-Wei Lin、Shiou-Ting Li、Chung-Yi Wu、Chi-Huey Wong

  DOI：10.1021/ja409097c

  日期：2013.10.16

  The structural diversity of glycoproteins often comes from post-translational glycosylation with heterogeneous N-glycans. Understanding the complexity of glycans related to various biochemical processes demands a well-defined synthetic sugar library. We report herein a unified convergent strategy for the rapid production of bi-, tri-, and tetra-antennary complex type N-glycans with and without terminal N-acetylneuraminic acid residues connected via the alpha-2,6 or alpha-2,3 linkages. Moreover, using sialyltransferases to install sialic acid can minimize synthetic steps through the use of shared intermediates to simplify the complicated procedures associated with conventional sialic acid chemistry. Furthermore, these synthetic complex oligosaccharides were compiled to create a glycan array for the profiling of HIV-1 broadly neutralizing antibodies PG9 and PG16 that were isolated from HIV infected donors. From the study of antibody PG16, we identified potential natural and unnatural glycan ligands, which may facilitate the design of carbohydrate-based immunogens and hasten the HIV vaccine development.