2-azidoethyl 2,3,4,6-tetra-O-acetyl-β-lactopyranoside | 230286-10-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-azidoethyl 2,3,4,6-tetra-O-acetyl-β-lactopyranoside
• 英文别名: 2-azidoethyl 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside；2-azidoethyl (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1-4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside；2-azidooethyl-2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside；2-Azidoethyl beta-D-lactoside heptaacetate；[(2R,3R,4S,5R,6R)-4,5-diacetyloxy-6-(2-azidoethoxy)-3-[(2S,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl acetate
• CAS: 230286-10-9
• 化学式: C₂₈H₃₉N₃O₁₈
• 分子量: 705.627
• InChiKey: QHXCYNJTYLXOSZ-HHZNOXSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  49
• 可旋转键数：
  22
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  235
• 氢给体数：
  0
• 氢受体数：
  20

反应信息

• 作为反应物：
  描述：

  2-azidoethyl 2,3,4,6-tetra-O-acetyl-β-lactopyranoside 在 palladium on activated charcoal 吡啶 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.0h， 生成 (N-9-Z-octadecenoyl-2-aminoethyl) 4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2,3,6-tri-O-acetyl-β-D-glucopyranoside
  参考文献：
  名称：

  An Improved Synthetic Procedure for the Preparation of N‐Acyl (2‐aminoethyl)‐β‐d‐glycopyranoside Lipids and Characterization of Their Mesogenic Properties

  摘要：

  A modified synthetic procedure was used for the synthesis of N-acyl (2-aminoethyl) glycosides bearing lactose, maltose, and melibiose carbohydrate headgroups and different acyl chains. The lipid glycosides were prepared in gram scale and investigated for their liquid crystalline properties. It was found that the polar spacer suppresses polymorphism, and the resulting simplified phase behavior was found in the pure state upon heating, as well as for the lyotropic phases.

  DOI：

  10.1080/07328300601082385
• 作为产物：
  描述：

  1',2',3',6',2,3,4,6-octa-O-acetyl-β-D-lactose 在 sodium azide 、 三氟化硼乙醚 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 41.5h， 生成 2-azidoethyl 2,3,4,6-tetra-O-acetyl-β-lactopyranoside
  参考文献：
  名称：

  Lactose-appended schizophyllan is a potential candidate as a hepatocyte-targeted antisense carrier

  摘要：

  一种携带乳糖附属物的裂殖酵母聚糖（β-1,3-葡聚糖）衍生物通过还原氨基化制备，可以与多核苷酸形成稳定的大分子复合物，表现出与乳糖结合凝集素的优良亲和力，并有效介导基因转染进入肝细胞。

  DOI：

  10.1039/b313426a

文献信息

• Preparation of aminoethyl glycosides for glycoconjugation
  作者：Robert Šardzík、Gavin T Noble、Martin J Weissenborn、Andrew Martin、Simon J Webb、Sabine L Flitsch

  DOI：10.3762/bjoc.6.81

  日期：——

  The synthesis of a number of aminoethyl glycosides of cell-surface carbohydrates, which are important intermediates for glycoarray synthesis, is described. A set of protocols was developed which provide these intermediates, in a short number of steps, from commercially available starting materials.

  描述了细胞表面碳水化合物的许多氨基乙基糖苷的合成，它们是 glycoarray 合成的重要中间体。开发了一套方案，这些方案可以在很短的步骤中从市售的起始材料中提供这些中间体。
• Schizophyllans carrying oligosaccharide appendages as potential candidates for cell-targeted antisense carrier
  作者：Teruaki Hasegawa、Tomohisa Fujisawa、Munenori Numata、Takahiro Matsumoto、Mariko Umeda、Ryouji Karinaga、Masami Mizu、Kazuya Koumoto、Taro Kimura、Shiro Okumura、Kazuo Sakurai、Seiji Shinkai

  DOI：10.1039/b412124b

  日期：——

  Schizophyllans carrying β-lactoside and α-mannoside appendages were prepared from native schizophyllan through NaIO4 oxidation followed by reductive amination using aminoethyl-β-lactoside and α-mannoside, respectively. The resulting schizophyllans form stable macromolecular complexes with polynucleotides, such as poly(C) and poly(dA). Specific affinity between these macromolecular complexes and saccharide-binding proteins was demonstrated by surface plasmon resonance and agarose gel staining assays. β-Lactoside-appended schizophyllan enhanced an antisense activity in hepatocytes which express lactoside-binding proteins on their cell surfaces.

  通过NaIO4氧化原生裂褶菌多糖，随后分别使用氨基乙基-β-半乳糖苷和α-甘露糖苷进行还原胺化反应，制备了带有β-半乳糖苷和α-甘露糖苷侧链的裂褶菌多糖。由此得到的裂褶菌多糖能与多聚核苷酸（如聚胞苷酸和聚dA）形成稳定的巨分子复合物。通过表面等离子体共振和琼脂糖凝胶染色实验，证明了这些巨分子复合物与糖结合蛋白之间存在特定的亲和力。带有β-半乳糖苷侧链的裂褶菌多糖增强了表达细胞表面半乳糖苷结合蛋白的肝细胞中的反义活性。
• Synthesis and antibacterial activities of novel tyrocidine A glycosylated derivatives towards multidrug-resistant pathogens
  作者：Yan Zou、Qingjie Zhao、Chunmei Zhang、Liang Wang、Wenjuan Li、Xiang Li、Qiuye Wu、Honggang Hu

  DOI：10.1002/psc.2774

  日期：2015.7

  and functions of peptides and plays a critical role in interacting with or binding to the target molecules. Herein, based on the previously reported method for macrocyclic glycopeptide synthesis, two series of tyrocidine A glycosylated derivatives (1a–f and 2a–f) were synthesized and evaluated for their antibacterial activities to further study the structure and activity relationships (SAR). Biological

  糖基化可以对肽的性质和功能产生多方面的影响，并且在与靶分子相互作用或结合中起关键作用。在此，根据先前报道的大环糖肽合成方法，合成了两个系列的酪氨酸A糖基化衍生物（1a-f和2a-f），并对其抗菌活性进行了评估，以进一步研究其结构和活性关系（SAR）。生物学研究表明，合成的糖基化衍生物对耐甲氧西林的金黄色葡萄球菌和耐万古霉素的肠球菌具有良好的抗菌活性。。SAR研究基于各种聚糖和键联来增强生化特性，从而鉴定出几种有效的抗生素，例如1f，其治疗指数比酪氨酸A大为改善。版权所有©2015欧洲肽协会和John Wiley＆Sons ，Ltd.
• Modular Synthesis of Amphiphilic Janus Glycodendrimers and Their Self-Assembly into Glycodendrimersomes and Other Complex Architectures with Bioactivity to Biomedically Relevant Lectins
  作者：Virgil Percec、Pawaret Leowanawat、Hao-Jan Sun、Oleg Kulikov、Christopher D. Nusbaum、Tam M. Tran、Annabelle Bertin、Daniela A. Wilson、Mihai Peterca、Shaodong Zhang、Neha P. Kamat、Kevin Vargo、Diana Moock、Eric D. Johnston、Daniel A. Hammer、Darrin J. Pochan、Yingchao Chen、Yoann M. Chabre、Tze C. Shiao、Milan Bergeron-Brlek、Sabine André、René Roy、Hans-J. Gabius、Paul A. Heiney

  DOI：10.1021/ja403323y

  日期：2013.6.19

  libraries containing 51 self-assembling amphiphilic Janus dendrimers with the monosaccharides D-mannose and D-galactose and the disaccharide D-lactose in their hydrophilic part is reported. These unprecedented sugar-containing dendrimers are named amphiphilic Janus glycodendrimers. Their self-assembly by simple injection of THF or ethanol solution into water or buffer and by hydration was analyzed by a combination

  报告了 7 个文库的模块化合成，该文库包含 51 个自组装两亲两性树枝状聚合物，其亲水部分含有单糖 D-甘露糖和 D-半乳糖以及双糖 D-乳糖。这些史无前例的含糖树枝状聚合物被命名为两亲性 Janus 树枝状聚合物。它们通过简单地将 THF 或乙醇溶液注入水或缓冲液中并通过水合进行自组装，通过动态光散射、共聚焦显微镜、低温透射电子显微镜、傅里叶变换分析和微量吸管抽吸实验等方法的组合进行分析，以评估机械性能。这些文库揭示了硬和软组件的多样性，包括单层球形、多边形和管状囊泡，称为糖树体，Janus glycodendrimer 和棒状胶束的聚集体称为 glycodendrimer 聚集体和 glycodendrimermicelles，cubosomes 表示 glycodendrimercubosomes 和固体薄片。这些组件在水中和缓冲液中随着时间的推移是稳定的，表现出窄的分子量分布，并显
• Preparation of oligosaccharides by homogenous enzymatic synthesis and solid phase extraction
  作者：Wenjun Wang、Chen Jin、Lina Guo、Yu Liu、Yue Wan、Xin Wang、Lei Li、Wei Zhao、Peng George Wang

  DOI：10.1039/c1cc13293h

  日期：——

  This communication describes a method for enzymatic preparation of bioactive glycans, which integrated the high-efficiency of homogenous phase enzymatic reaction and fast separation of solid phase extraction.

  该交流描述了一种酶法制备生物活性聚糖的方法，该方法集高效率的均相酶促反应和固相萃取的快速分离于一体。