p-Cyanophenyl-β-D-glucopyranosid | 28217-36-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-Cyanophenyl-β-D-glucopyranosid
• 英文别名: 4-cyanophenyl β-D-glucopyranoside；4β-D-glucopyranosyloxy-benzonitrile；4-(beta-D-Glucopyranosyloxy)benzonitrile；4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybenzonitrile
• CAS: 28217-36-9
• 化学式: C₁₃H₁₅NO₆
• 分子量: 281.265
• InChiKey: SREVUBGNIJBKIT-UJPOAAIJSA-N

物化性质

• 熔点：
  185-187 °C(Solv: ethanol (64-17-5))
• 沸点：
  569.7±50.0 °C(Predicted)
• 密度：
  1.52±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  123
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  α-galactosyl fluoride 、 p-Cyanophenyl-β-D-glucopyranosid 在 E338 mutant TtβGly glycosidase from Thermus thermophilus 作用下， 反应 12.0h， 以85%的产率得到4-cyanophenyl β-D-galactopyranosyl-(1->3)-β-D-glucopyranoside
  参考文献：
  名称：

  Engineering of glucoside acceptors for the regioselective synthesis of β-(1→3)-disaccharides with glycosynthases

  摘要：

  Glycosynthase mutants obtained from Thermotoga maritima were able to catalyze the regioselective synthesis of aryl beta-D-Galp-(1 -> 3)-beta-D-Glcp and aryl beta-D-Glcp-(1 -> 3)-beta-D-Glcp in high yields (up to 90 %) using aryl beta-D-glucosides as acceptors. The need for an aglyconic aryl group was rationalized by molecular modeling calculations, which have emphasized a high stabilizing interaction of this group by stacking with W312 of the enzyme. Unfortunately, the deprotection of the aromatic group of the disaccharides was not possible without partial hydrolysis of the glycosidic bond. The replacement of aryl groups by benzyl ones could offer the opportunity to deprotect the anomeric position under very mild conditions. Assuming that benzyl acceptors could preserve the stabilizing stacking, benzyl beta-D-glucoside firstly assayed as acceptor resulted in both poor yields and poor regioselectivity. Thus, we decided to undertake molecular modeling calculations in order to design which suitable substituted benzyl acceptors could be used. This study resulted in the choice of 2-biphenylmethyl beta-D-glucopyranoside. This choice was validated experimentally, since the corresponding beta-(1 -> 3) disaccharide was obtained in good yields and with a high regioselectivity. At the same time, we have shown that phenyl 1-thio-beta-D-glucopyranoside was also an excellent substrate leading to similar results as those obtained with the O-phenyl analogue. The NBS deprotection of the S-phenyl group afforded the corresponding disaccharide quantitatively. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.07.018
• 作为产物：
  描述：

  4-Cyanophenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 在 甲醇 、 sodium methylate 作用下， 生成 p-Cyanophenyl-β-D-glucopyranosid
  参考文献：
  名称：

  Nath; Rydon, Biochemical Journal, 1954, vol. 57, p. 1,2

  摘要：

  DOI：

文献信息

• Rapid phenolic O-glycosylation of small molecules and complex unprotected peptides in aqueous solvent
  作者：Tyler J. Wadzinski、Angela Steinauer、Liana Hie、Guillaume Pelletier、Alanna Schepartz、Scott J. Miller

  DOI：10.1038/s41557-018-0041-8

  日期：2018.6

  Glycosylated natural products and synthetic glycopeptides represent a significant and growing source of biochemical probes and therapeutic agents. However, methods that enable the aqueous glycosylation of endogenous amino acid functionality in peptides without the use of protecting groups are scarce. Here, we report a transformation that facilitates the efficient aqueous O-glycosylation of phenolic

  糖基化的天然产物和合成的糖肽代表了生化探针和治疗剂的重要且不断增长的来源。然而，缺少能够在不使用保护基的情况下使肽中的内源氨基酸官能团进行水性糖基化的方法。在这里，我们报道了一种转化，该转化促进了在广泛的小分子，未保护的酪氨酸和嵌入一系列复杂，完全未保护的肽中的酪氨酸残基的酚官能团的有效O-糖基化水溶液。该转化使用糖基氟化物供体，并由Ca（OH）2促进，取决于糖基供体的立体化学，在室温下在水中迅速进行，并具有良好的收率和选择性形成独特的异头物产物。观察到高官能团耐受性，并且在几乎所有蛋白原性氨基酸的所有侧链均存在的情况下，Cys例外，酚糖基化选择性发生。该方法为水中的O-芳基糖苷和Tyr- O-糖基化肽的无保护基的合成提供了高度选择性，有效且操作简单的方法。