2-(β-glucosyloxy)ethyl methacrylate | 47087-43-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(β-glucosyloxy)ethyl methacrylate
• 英文别名: 2-(beta-d-Glucosyloxy)ethyl methacrylate；2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyethyl 2-methylprop-2-enoate
• CAS: 47087-43-4
• 化学式: C₁₂H₂₀O₈
• 分子量: 292.286
• InChiKey: KUQRLZZWFINMDP-WSOSLHDDSA-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：

  α-环糊精 、 2-(β-glucosyloxy)ethyl methacrylate 在 cyclodextrin glycosyltransferase from Bacillus macerans 作用下， 以 aq. buffer 为溶剂， 生成 Glc-α-Glc-β-ethyl methacrylate 、 (Glc-α)₂-Glc-β-ethyl methacrylate 、 (Glc-α)₃-Glc-β-ethyl methacrylate
  参考文献：
  名称：

  从淀粉和α-环糊精的生物催化合成麦芽糊精基丙烯酸酯。

  摘要：

  通过CGTase成功地由Macerans芽孢杆菌CGTase合成了新型2-（β-低聚丙氧基）-（甲基）丙烯酸乙酯单体，催化了2-（β-葡糖氧基）-丙烯酸乙酯和甲基丙烯酸与α-环糊精或淀粉的偶联。HPLC-UV分析表明，CGTase催化的反应生成具有1至15个吡喃葡萄糖基单元的2-（β-麦芽低聚氧基）-丙烯酸乙酯。1 H NMR光谱显示，在CGTase催化的偶联反应过程中，受体分子中的β-键得以保留，而新引入的葡萄糖单元则通过α-（1,4）-糖苷键连接。合成的2-（β-低聚丙氧基）-丙烯酸乙酯单体通过水性自由基聚合成功聚合，得到梳形的糖聚合物聚（2-（β-低聚丙氧基）-丙烯酸乙酯）。

  DOI：

  10.1002/mabi.201400091
• 作为产物：
  描述：

  甲基丙烯酸羟乙酯 在 3 A molecular sieve 、 sodium methylate 、 silver trifluoromethanesulfonate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 48.67h， 生成 2-(β-glucosyloxy)ethyl methacrylate
  参考文献：
  名称：

  Ambrosi, Moira; Batsanov, Andrei S.; Cameron, Neil R., Journal of the Chemical Society. Perkin Transactions 1 (2001), 2002, # 1, p. 45 - 52

  摘要：

  DOI：

文献信息

• Enzymatic Synthesis of 2-(β-Galactosyl)-ethyl Methacrylate by β-Galactosidase from <i>Pyrococcus woesei</i> and Application for Glycopolymer Synthesis and Lectin Studies
  作者：Marius Hoffmann、Elisabeth Gau、Susanne Braun、Andrij Pich、Lothar Elling

  DOI：10.1021/acs.biomac.9b01647

  日期：2020.2.10

  for the synthesis of glycosides by transglycosylation reactions. Especially glycosidases from hyperthermophilic bacteria are useful for reactions under extreme reaction conditions, e.g., in the presence of organic solvents. We herein report the facile enzymatic synthesis and purification of 2-(β-galactosyl)-ethyl methacrylate (Gal-EMA) with the recombinant hyperthermostable glycosidase from Pyrococcus

  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
• Chemo-enzymatic synthesis route to poly(glucosyl-acrylates) using glucosidase from almonds
  作者：Wouter M. J. Kloosterman、Steven Roest、Siti R. Priatna、Erythrina Stavila、Katja Loos

  DOI：10.1039/c3gc41115j

  日期：——

  Novel types of glucosyl-acrylate monomers are obtained by β-glucosidase from almond catalyzed glycosidation reaction. The saccharide-acrylate monomers were synthesized by reaction of D-glucose with hydroxyl functional acrylates: 2-hydroxyethyl acrylate (2-HEA), 2-hydroxyethyl methacrylate (2-HEMA) and 4-hydroxybutyl acrylate (4-HBA). The reaction products could be identified as 2-(β-glucosyloxy)-ethyl acrylate, 2-(β-glucosyloxy)-ethyl methacrylate and 4-(β-glucosyloxy)-ethyl acrylate respectively. The synthesis yield was optimized by variation of the 2-HEA–water ratio, the presence of water-miscible co-solvents and the reaction time. The optimal reaction mixture was found to contain 13 vol% water, 80 vol% 2-HEA and 7 vol%; 1.4-dioxane. The maximal yield under these conditions was 50 wt% based on D-glucose after 24 hours of reaction. The enzymatically synthesized glucosyl-acrylates were successfully polymerized by free radical polymerization in DMF and water. The glycosidic linkage of the glycosyl-acrylate monomers was retained during the polymerization process. The enzymatically synthesized glucosyl-acrylates could be successfully copolymerized with vinyl monomers 2-HEA, 2-HEMA, methacryl amide and N-vinyl imidazole.

  β-葡萄糖苷酶从杏仁催化的糖苷化反应中获得了新型的葡萄糖基丙烯酸酯单体。糖基丙烯酸酯单体是通过 D-葡萄糖与羟基功能丙烯酸酯反应合成的：2-羟乙基丙烯酸酯（2-HEA）、2-羟乙基甲基丙烯酸酯（2-HEMA）和 4-羟丁基丙烯酸酯（4-HBA）。反应产物可分别鉴定为 2-(β-葡萄糖酰氧基)-丙烯酸乙酯、2-(β-葡萄糖酰氧基)-甲基丙烯酸乙酯和 4-(β-葡萄糖酰氧基)-丙烯酸乙酯。通过改变 2-HEA 与水的比例、水混溶助溶剂的存在和反应时间，对合成产率进行了优化。结果发现，最佳反应混合物中水的含量为 13%，2-HEA 的含量为 80%，1.4-二氧六环的含量为 7%。在这些条件下，反应 24 小时后，D-葡萄糖的最大产量为 50 wt%。酶法合成的葡萄糖基丙烯酸酯在 DMF 和水中通过自由基聚合反应成功聚合。糖基丙烯酸酯单体的糖苷键在聚合过程中得以保留。酶法合成的葡萄糖基丙烯酸酯可成功地与乙烯基单体 2-HEA、2-HEMA、甲基丙烯酸酰胺和 N-乙烯基咪唑共聚。
• 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.
• PROCESS FOR PRODUCING GLYCOSIDES OF ACRYLATE DERIVATIVES EMPLOYING SACCHARIDES AND GLYCOSIDASES
  申请人：BASF SE

  公开号：EP2598647A1

  公开（公告）日：2013-06-05
• ENZYMATIC PRODUCTION OF AN ETHYLENICALLY UNSATURATED GLYCOSIDE
  申请人：KELLER Harald

  公开号：US20120028308A1

  公开（公告）日：2012-02-02

  Ethylenically unsaturated glycosides of formula I wherein n, A, X, R 3 and R 4 have the meanings given in the description are produced by reacting an ethylenically unsaturated alcohol of formula II with a saccharide of formula III in the presence of a glycosidase, such as an amylase, cellulase, glucosidase or galactosidase, (i) at a molar ratio of ethylenically unsaturated alcohol of formula II to saccharide of formula III of from 2:1 to 30:1; (ii) in the presence of a solvent mixture of water and a water miscible organic solvent that is no primary or secondary alcohol, such as acetone, acetonitrile, t-pentanol, t-butanol, 1,4 -dioxane and tetrahydrofuran, at a weight ratio of water to organic solvent of from 0.1:1 to 9:1 ; and (iii) at a weight ratio of solvent mixture to saccharide of from 3:1 to 30:1.