2-acrylaminoethyl lactoside | 443770-02-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-acrylaminoethyl lactoside
• 英文别名: 2-acryloyl-aminoethyl (β-D-galactopyranosyl)-(1-4)-β-D-glucopyranoside；2-(N-acryloylamino)ethyl (β-D-galactopyranosyl)-(1->4)-β-D-glucopyranoside；N-[2-[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxyethyl]prop-2-enamide
• CAS: 443770-02-3
• 化学式: C₁₇H₂₉NO₁₂
• 分子量: 439.417
• InChiKey: SMWSNCYUKWOZSQ-VTEGJVQPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.3
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  208
• 氢给体数：
  8
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  1',2',3',6',2,3,4,6-octa-O-acetyl-β-D-lactose 在 Adam’s catalyst 三氟化硼乙醚 、 氢气 、 sodium methylate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 氯仿 为溶剂， 反应 21.0h， 生成 2-acrylaminoethyl lactoside
  参考文献：
  名称：

  Design and Synthesis of Biotin Chain-Terminated Glycopolymers for Surface Glycoengineering

  摘要：

  Biotin chain-terminated glycopolymers were generated by cyanoxyl-mediated free-radical polymerization using a biotin-derivatized arylamine initiator with high conversion (75%) and low polydispersity (1.30). Streptavidin-biotinylated glycopolymer binding was verified by SDS-PAGE gel shift assay and patterned glycocalyx-mimetic surfaces successfully fabricated.

  DOI：

  10.1021/ja025788v

文献信息

• One-pot chemoenzymatic synthesis of glycopolymers from unprotected sugars <i>via</i> glycosidase-catalysed glycosylation using triazinyl glycosides
  作者：Tomonari Tanaka、Ayane Matsuura、Yuji Aso、Hitomi Ohara

  DOI：10.1039/d0cc02838j

  日期：——

  Glycopolymers were successfully synthesised from unprotected sugars in aqueous media via a one-pot chemoenzymatic process of three reactions; the direct synthesis of 4,6-dimethoxy-1,3,5-triazin-2-yl glycosides from unprotected sugars, a glycosidase-catalysed glycosylation using the triazinyl glycoside to afford glycomonomers and a radical polymerisation. The resulting glycopolymers exhibited specific

  通过三个反应的一锅化学酶法，成功地在水性介质中由未保护的糖合成了糖共聚物。由未保护的糖直接合成4,6-二甲氧基-1,3,5-三嗪-2-基糖苷，使用三嗪基糖苷进行糖苷酶催化的糖基化反应以提供糖单体和自由基聚合。所得的糖聚合物表现出与相应的凝集素作为糖簇的特异性相互作用。
• Investigating Cell Surface Galectin-Mediated Cross-Linking on Glycoengineered Cells
  作者：Brian Belardi、Geoff P. O’Donoghue、Adam W. Smith、Jay T. Groves、Carolyn R. Bertozzi

  DOI：10.1021/ja301694s

  日期：2012.6.13

  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.