2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1-4)-1,2,3,6-tetra-O-benzoyl-D-glucopyranosyl trichloroacetimidate | 736969-78-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1-4)-1,2,3,6-tetra-O-benzoyl-D-glucopyranosyl trichloroacetimidate
• 英文别名: [(2R,3R,4S,5R)-4,5-dibenzoyloxy-3-[(2S,3R,4S,5R,6R)-3,4,5-tribenzoyloxy-6-(benzoyloxymethyl)oxan-2-yl]oxy-6-(2,2,2-trichloroethanimidoyl)oxyoxan-2-yl]methyl benzoate
• CAS: 736969-78-1
• 化学式: C₆₃H₅₀Cl₃NO₁₈
• 分子量: 1215.44
• InChiKey: HUCNKFYJQPVDLI-ZWRMCBPTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.03
• 重原子数：
  85.0
• 可旋转键数：
  19.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  244.87
• 氢给体数：
  1.0
• 氢受体数：
  19.0

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1-4)-1,2,3,6-tetra-O-benzoyl-D-glucopyranosyl trichloroacetimidate 、 N-羟乙基丙烯酰胺 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 2.03h， 以65%的产率得到2-(N-acryloylamino)ethyl (2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzoyl-β-D-glucopyranoside
  参考文献：
  名称：

  Investigating Cell Surface Galectin-Mediated Cross-Linking on Glycoengineered Cells

  摘要：

  The galectin family of glycan-binding proteins is thought to mediate many cellular processes by oligomerizing cell surface glycoproteins and glycolipids into higher-order aggregates. This hypothesis reflects the known oligomeric states of the galectins themselves and their binding properties with multivalent ligands in vitro, but direct evidence of their ability to cross-link ligands on a cell surface is lacking. A major challenge in fundamental studies of galectin ligand interactions is that their natural ligands comprise a heterogeneous collection of glyco-conjugates that share related glycan structures but disparate underlying scaffolds. Consequently, there is no obvious means to selectively monitor the behaviors of natural galectin ligands on live cell surfaces. Here we describe an approach for probing the galectin-induced multimerization of glycoconjugates on cultured cells. Using RAFT polymerization, we synthesized well-defined glycopolymers (GPs) functionalized with galectin-binding glycans along the backbone, a lipid group on one end and a fluorophore on the other. After insertion into live cell membranes, the GPs' fluorescence lifetime and diffusion time were measured in the presence and absence of galectin-1. We observed direct evidence for galectin-1-mediated extended cross-linking on the engineered cells, a phenomenon that was dependent on glycan structure. This platform offers a new approach to exploring the "galectin lattice" hypothesis and to defining galectin ligand specificity in a physiologically relevant context.

  DOI：

  10.1021/ja301694s
• 作为产物：
  描述：

  2,3,6-O-tri-Benzoyl-4-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-D-glucopyranoside 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三氯乙腈 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以65%的产率得到2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1-4)-1,2,3,6-tetra-O-benzoyl-D-glucopyranosyl trichloroacetimidate
  参考文献：
  名称：

  EP1792620

  摘要：

  公开号：

文献信息

• [EN] NOVEL SULFATED OLIGOSACCHARIDE DERIVATIVES<br/>[FR] NOUVEAUX DÉRIVÉS D'OLIGOSACCHARIDES SULFATÉS
  申请人：PROGEN PHARMACEUTICALS LTD

  公开号：WO2009049370A1

  公开（公告）日：2009-04-23

  The invention relates to novel compounds that have utility as inhibitors of heparan sulfate-binding proteins; compositions comprising the compounds, and use of the compounds and compositions thereof for the antiangiogenic, antimetastatic, anti-inflammatory, antimicrobial, anticoagulant and/or antithrombotic treatment of a mammalian subject.

  这项发明涉及具有作为肝素硫酸结合蛋白抑制剂的效用的新化合物；包含这些化合物的组合物；以及利用这些化合物和组合物对哺乳动物主体进行抗血管生成、抗转移、抗炎、抗微生物、抗凝血和/或抗血栓治疗的用途。
• Synthesis of Diverse Seleno‐Glycolipids <i>via</i> the Transacetalization of Selenoacetals
  作者：Hayata Fukuo、Tatsuya Suzuki、Junpei Shimabukuro、Naoko Komura、Hide‐Nori Tanaka、Akihiro Imamura、Hideharu Ishida、Hiromune Ando

  DOI：10.1002/ejoc.202100847

  日期：2021.10.26

  membrane proteins. To expand the scope of available seleno-glycolipids, we established a facile synthesis toward novel mono- and diseleno-glycolipids with various glycan and lipid moieties; this proceeds via transacetalization of selenoacetals and glycosyl imidates. This work demonstrates the first synthesis of diseleno-glycolipids.

  硒糖脂是用于膜蛋白 X 射线结构研究的有吸引力的去污剂。为了扩大可用硒糖脂的范围，我们建立了对具有各种聚糖和脂质部分的新型单和二硒糖脂的简便合成；这通过硒缩醛和糖基亚氨酸酯的转缩醛化进行。这项工作证明了二硒糖脂的首次合成。
• VaporSPOT: Parallel Synthesis of Oligosaccharides on Membranes
  作者：Alexandra Tsouka、Pietro Dallabernardina、Marco Mende、Eric T. Sletten、Sabrina Leichnitz、Klaus Bienert、Kim Le Mai Hoang、Peter H. Seeberger、Felix F. Loeffler

  DOI：10.1021/jacs.2c07285

  日期：2022.11.2

  Automated chemical synthesis has revolutionized synthetic access to biopolymers in terms of simplicity and speed. While automated oligosaccharide synthesis has become faster and more versatile, the parallel synthesis of oligosaccharides is not yet possible. Here, a chemical vapor glycosylation strategy (VaporSPOT) is described that enables the simultaneous synthesis of oligosaccharides on a cellulose membrane

  自动化化学合成在简单性和速度方面彻底改变了生物聚合物的合成途径。虽然自动化低聚糖合成变得更快和更通用，但寡糖的平行合成尚不可能。在这里，描述了一种化学气相糖基化策略 (VaporSPOT)，它能够在纤维素膜固体支持物上同时合成低聚糖。不同的接头允许对目标寡糖进行灵活和直接的切割、纯化和表征。该方法是开发并行自动聚糖合成平台的基础。