5-azidopentyl-O-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside | 1169693-80-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-azidopentyl-O-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside
• 英文别名: 5-azidopentyl 3,6-di-O-benzyl-2-deoxy-2-phthalamido-β-D-glucopyranoside；2-[(2R,3R,4R,5S,6R)-2-(5-azidopentoxy)-5-hydroxy-4-phenylmethoxy-6-(phenylmethoxymethyl)oxan-3-yl]isoindole-1,3-dione
• CAS: 1169693-80-4
• 化学式: C₃₃H₃₆N₄O₇
• 分子量: 600.671
• InChiKey: APVUQJCWNVFXFK-XSETXXIFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  44
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  5-azidopentyl-O-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 、 p-tolyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以75%的产率得到5-azidopentyl-O-3-O-benzyl-4,6-O-benzylidene-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：

  Efficient Convergent Synthesis of Bi-, Tri-, and Tetra-antennary Complex Type N-Glycans and Their HIV-1 Antigenicity

  摘要：

  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.

  DOI：

  10.1021/ja409097c
• 作为产物：
  描述：

  p-tolyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside 在 三乙基硅烷 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 5-azidopentyl-O-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside
  参考文献：
  名称：

  Efficient Convergent Synthesis of Bi-, Tri-, and Tetra-antennary Complex Type N-Glycans and Their HIV-1 Antigenicity

  摘要：

  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.

  DOI：

  10.1021/ja409097c

文献信息

• Highly Alpha-Selective Sialyl Phosphate Donors for Efficient Preparation of Natural Sialosides
  作者：Che-Hsiung Hsu、Kuo-Ching Chu、Yih-Shyan Lin、Jeng-Liang Han、Yu-Shiang Peng、Chien-Tai Ren、Chung-Yi Wu、Chi-Huey Wong

  DOI：10.1002/chem.200903035

  日期：2010.2.8

  Hubble, bubble, toil, and trouble: The use of a new sialyl phosphate donor allows the stereoselective, one‐pot multicomponent synthesis of α‐sialooligosaccharides (see scheme).

  哈勃，气泡，辛劳和麻烦：使用新的唾液酸磷酸酯供体可以立体选择性地单锅多组分合成α-唾液寡糖（参见方案）。
• Monitoring Glycan–Protein Interactions by NMR Spectroscopic Analysis: A Simple Chemical Tag That Mimics Natural CH–π Interactions
  作者：Luis P. Calle、Begoña Echeverria、Antonio Franconetti、Sonia Serna、M. Carmen Fernández‐Alonso、Tammo Diercks、F. Javier Cañada、Ana Ardá、Niels‐Christian Reichardt、Jesús Jiménez‐Barbero

  DOI：10.1002/chem.201501248

  日期：2015.8.3

  propose the difluoroacetamide moiety (an acetamide bioisoster) as a novel tag for detecting by NMR analysis those glycan–protein interactions that involve N‐acetylated sugars. Although difluoroacetamide has been used previously as a substituent in medicinal chemistry, here we employ it as a specific sensor to monitor interactions between GlcNAc‐containing glycans and a model lectin (wheat germ agglutinin)

  分子识别过程的检测需要鲁棒，特定且易于实现的传感方法，尤其是对于筛选应用。在这里，我们提出了二氟乙酰胺部分（乙酰胺生物甾醇）作为一种新型标签，用于通过NMR分析检测涉及N-乙酰化糖类的糖蛋白相互作用。尽管二氟乙酰胺以前曾在药物化学中用作取代基，但在这里我们将其用作监测含GlcNAc的聚糖与模型凝集素（小麦胚芽凝集素）之间相互作用的特异传感器。与广泛使用的三氟乙酰胺基相反，二氟乙酰胺标签包含双子1 H和19 F原子，允许1 H和19F NMR方法可轻松，可靠地检测涉及一系列结合亲和力的GlcNAc-（或GalNAc-）部分的分子识别过程。CHF 2 CONH-部分的行为与所涉及的芳族糖相互作用中的天然乙酰胺片段非常相似，提供相似的结合能和构象，而全氟化CF 3 CONH-类似物的区别则更大。
• Construction of<i>N</i>-Glycan Microarrays by Using Modular Synthesis and On-Chip Nanoscale Enzymatic Glycosylation
  作者：Sonia Serna、Juan Etxebarria、Nerea Ruiz、Manuel Martin-Lomas、Niels-Christian Reichardt

  DOI：10.1002/chem.201001295

  日期：2010.11.22

  An effective chemoenzymatic strategy is reported that has allowed the construction, for the first time, of a focused microarray of synthetic N‐glycans. Based on modular approaches, a variety of N‐glycan core structures have been chemically synthesized and covalently immobilized on a glass surface. The printed structures were then enzymatically diversified by the action of three different glycosyltransferases

  据报道，一种有效的化学酶策略首次允许构建合成的N-聚糖聚焦微阵列。基于模块化方法，各种N‐聚糖核心结构已化学合成并共价固定在玻璃表面上。然后，通过印刷机器人，通过置于微阵列各个点顶部的纳米液滴中的三种不同糖基转移酶的作用，使印刷的结构酶促多样化。转化之后是对末端糖具有特异性的凝集素结合。与溶液相中进行的反应相比，纳米液滴中表面结合配体的这种酶促延伸将所需的珍贵糖基转移酶的数量减少了七个数量级。此外，仅可以选择已显示为特定糖基转移酶底物的那些配体以在阵列上延伸。这里描述的方法，
• Differential Receptor Binding Affinities of Influenza Hemagglutinins on Glycan Arrays
  作者：Hsin-Yu Liao、Che-Hsiung Hsu、Shih-Chi Wang、Chi-Hui Liang、Hsin-Yung Yen、Ching-Yao Su、Chien-Hung Chen、Jia-Tsrong Jan、Chien-Tai Ren、Chung-Hsuan Chen、Ting-Jen R. Cheng、Chung-Yi Wu、Chi-Huey Wong

  DOI：10.1021/ja104657b

  日期：2010.10.27

  A library of 27 sialosides, including seventeen 2,3-linked and ten 2,6-linked glycans, has been prepared to construct a glycan array and used to profile the binding specificity of different influenza hemagglutinins (HA) subtypes, especially from the 2009 swine-originated H1N1 and seasonal influenza viruses. It was found that the HAs from the 2009 H1N1 and the seasonal Brisbane strain share similar binding profiles yet different binding affinities toward various alpha 2,6 sialosides. Analysis of the binding profiles of different HA subtypes indicate that a minimum set of 5 oligosaccharides can be used to differentiate influenza H1, H3, H5, H7, and H9 subtypes. In addition, the glycan array was used to profile the binding pattern of different influenza viruses. It was found that most binding patterns of viruses and HA proteins are similar and that glycosylation at Asn27 is essential for receptor binding.
• Synthesis of a core trisaccharide building block for the assembly of N-glycan neoconjugates
  作者：Sonia Serna、Bharat Kardak、Niels-Christian Reichardt、Manuel Martin-Lomas

  DOI：10.1016/j.tetasy.2009.02.028

  日期：2009.5

  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.