2-(β-D-galactosyloxy)ethyl methacrylate | 21698-14-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(β-D-galactosyloxy)ethyl methacrylate
• 英文别名: 2-(beta-d-Galactosyloxy)ethyl methacrylate；2-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyethyl 2-methylprop-2-enoate
• CAS: 21698-14-6
• 化学式: C₁₂H₂₀O₈
• 分子量: 292.286
• InChiKey: KUQRLZZWFINMDP-KZFLBEFCSA-N

物化性质

• 沸点：
  490.3±45.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  126
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  P'-[2-(acetylamino)-2-deoxy-α-D-glucopyranosyl] ester uridine 5'-(trihydrogen diphosphate), disodium salt 、 2-(β-D-galactosyloxy)ethyl methacrylate 在 potassium chloride 、 recombinant β1,3-N-acetylglucosaminyltransferase from Helicobacter pylori 、 magnesium chloride 、 1,4-二巯基-2,3-丁二醇 、 alkaline phosphatase 作用下， 以 aq. phosphate buffer 为溶剂， 生成 N-acetylglucosaminyl β1,3-2-(β-galactosyl)ethyl methacrylate
  参考文献：
  名称：

  沃氏球菌β-半乳糖苷酶酶法合成2-（β-半乳糖基）-甲基丙烯酸甲酯及其在糖聚合物合成和凝集素研究中的应用。

  摘要：

  糖苷酶长期以来一直用于通过转糖基化反应合成糖苷。特别是来自嗜热细菌的糖苷酶可用于极端反应条件下的反应，例如在有机溶剂的存在下。我们在此报道了以高产率从重组火球菌得到的2-（β-半乳糖基）-甲基丙烯酸乙酯（Gal-EMA）的简便酶促合成和纯化。优化的反应条件导致了半乳糖基化单体的克级合成，转糖基化率为88％。Gal-EMA产物的特征在于高效液相色谱-电喷雾电离质谱（HPLC-ESI-MS），核磁共振（NMR）光谱和红外（IR）光谱。Gal-EMA用于合成糖官能化的丙烯酸酯聚合物，其中掺入了一定量的半乳糖（0-100％）。使用酶联凝集素测定（ELLA）分析来自蓖麻的凝集素RCA120与糖聚合物的结合亲和力，发现KD值介于0.24和6.2 nM之间，具体取决于掺入的Gal-EMA的量。Gal-EMA合成丙烯酸酯官能化的聚糖低聚物的潜力已通过两个糖基转移酶顺序延长末端半乳糖而得到证实，从而产生了末

  DOI：

  10.1021/acs.biomac.9b01647
• 作为产物：
  描述：

  beta-D-半乳糖五乙酸酯 在 三氟化硼乙醚 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 36.0h， 生成 2-(β-D-galactosyloxy)ethyl methacrylate
  参考文献：
  名称：

  Facile in situ preparation of biologically active multivalent glyconanoparticles

  摘要：

  生物活性多价糖纳米颗粒通过在HAuCl4水溶液中还原通过RAFT聚合制备的明确定义的糖聚合物，以一种极其简单的方法制备。

  DOI：

  10.1039/b608383h

文献信息

• CARBOHYDRATE-BASED COMPOSITIONS AND METHODS FOR TARGETED DRUG DELIVERY
  申请人：Stayton Patrick

  公开号：US20140235790A1

  公开（公告）日：2014-08-21

  Provided herein are compositions and methods for intracellular delivery. The compositions are polymer compositions in which the polymer serves as a carrier for therapeutic and/or diagnostic agents. The polymer compositions are effective in targeted delivery of therapeutic and/or diagnostic agents to a cell. The polymer compositions include a targeting moiety that includes carbohydrate groups that effectively target specific cell surface receptors. The polymer compositions also include an agent binding moiety that effectively associates the therapeutic and/or diagnostic agent to be delivered to the cell.

  本文提供了一种用于细胞内递送的组合物和方法。这些组合物是聚合物组合物，其中聚合物作为治疗和/或诊断试剂的载体。这些聚合物组合物在将治疗和/或诊断试剂有针对性地递送至细胞方面非常有效。这些聚合物组合物包括一个包含碳水化合物基团的靶向部分，有效地靶向特定的细胞表面受体。这些聚合物组合物还包括一个结合部分，有效地将待递送至细胞的治疗和/或诊断试剂与之结合。
• Investigation of the interaction between peanut agglutinin and synthetic glycopolymeric multivalent ligands
  作者：Moira Ambrosi、Neil R. Cameron、Benjamin G. Davis、Snjezana Stolnik

  DOI：10.1039/b411555b

  日期：——

  The interaction between synthetic glycoplymers bearing β-D-galactose side groups and the lectin peanut agglutinin (PNA) was investigated by UV-difference spectroscopy and isothermal titration calorimetry (ITC). UV-difference spectroscopy indicated that the polymer–lectin interaction was stronger than that between PNA and either the corresponding monomer, D-galactose or D-lactose. The thermodynamics of binding (K, ΔG, ΔH, ΔS and n) were determined from ITC data by fitting with a two-site, non-cooperative binding model. It was found that the glycopolymer displayed around a 50 times greater affinity for the lectin than the parent carbohydrate, and around 10 times greater than the monomer, on a valency-corrected basis. Binding was found to be entropically driven, and was accompanied by aggregation and precipitation of protein molecules. Furthermore, interesting differences between polymers prepared either from deacetylated monomers, or by deacetylation of pre-formed polymers, were found.

  通过紫外差光谱和等温滴定量热法 (ITC) 研究了带有 β-D-半乳糖侧基的合成糖聚合物与凝集素花生凝集素 (PNA) 之间的相互作用。紫外差光谱表明，聚合物与凝集素之间的相互作用强于 PNA 与相应单体 D-半乳糖或 D-乳糖之间的相互作用。结合热力学（K、ΔG、ΔH、ΔS 和 n）是通过拟合两位点非合作结合模型从 ITC 数据确定的。结果发现，在价态校正的基础上，糖聚合物对凝集素的亲和力比母体碳水化合物高约 50 倍，比单体高约 10 倍。发现结合是熵驱动的，并伴随着蛋白质分子的聚集和沉淀。此外，还发现了由脱乙酰单体制备的聚合物或通过预形成聚合物脱乙酰制备的聚合物之间的有趣差异。
• HETEROGENEOUS POLYMERIC MICELLES FOR INTRACELLULAR DELIVERY
  申请人：Johnson Paul

  公开号：US20120021514A1

  公开（公告）日：2012-01-26

  Compositions comprising a heterogeneous polymeric micelle and an agent (e.g., a polynucleotide) associated with the micelle are disclosed, together with methods for intracellular delivery of such agent.

  本发明揭示了包括异质性聚合物胶束和与该胶束相关联的剂（例如多核苷酸）的组合物，以及用于细胞内输送此类剂的方法。
• Glycosylation Using Unprotected Alkynyl Donors
  作者：Sreeman K. Mamidyala、M.G. Finn

  DOI：10.1021/jo901857x

  日期：2009.11.6

  Gold(III) activation of unprotected propargyl glycosyl donors has been shown to be effective for the synthesis of saccharides. Terminal propargyl glycosides of glucose, galactose, and mannose required heating at reflux in acetonitrile with 5% AuCl(3) for reaction with various primary alcohol acceptors, the latter used in 10-fold molar excess relative to donor. Donors containing the 2-butynyl group were more reactive, giving good yields of glycoside products at lower temperatures Secondary alcohols could also be used but with diminished efficiency. The propargylic family of donors is especially convenient because they can be easily prepared on large scale by Fischer glycosylation and stored indefinitely before chemoselective activation by the catalyst.
• Transglycosylation in a two-phase aqueous-organic system with catalysis by a lipid-coated β-d-galactosidase
  作者：Toshiaki Mori、Sanae Fujita、Yoshio Okahata

  DOI：10.1016/s0008-6215(96)00298-4

  日期：1997.2

  A lipid-coated beta-D-galactosidase was prepared in which the enzyme surface is covered with a lipid monolayer and two long alkyl lipophilic tails serve to solubilize the enzyme in organic solvents. In a two-phase aqueous-organic system, a lipid-coated enzyme exists in the organic (2-propyl ether) phase and acts as an efficient transgalactosylation catalyst for various hydrophobic alcohols with lactose in the aqueous buffer solution. When a native beta-D-galactosidase was employed in the two-phase system, neither the transgalactosylation nor the hydrolysis reaction proceeded due to denaturation of the enzyme at the interface, Effects of coating lipid molecules, origins of enzymes, reaction in organic solvents, and chemical structures of acceptor alcohols on the transgalactosylation catalyzed by the lipid-coated enzyme were studied. This system could also be applied in a large-scale synthesis on the 0.1-1 g scale. (C) 1997 Elsevier Science Ltd.