[4-(tetra-O-acetyl-β-D-glucopyranosyloxy)-phenyl]-acetic acid 2-cyanoethyl ester | 476330-48-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: [4-(tetra-O-acetyl-β-D-glucopyranosyloxy)-phenyl]-acetic acid 2-cyanoethyl ester
• 英文别名: [(4-tetra-O-acetyl-β-D-glucopyranosyloxy)phenyl]acetic acid 2-cyanoethyl ester
• CAS: 476330-48-0
• 化学式: C₂₅H₂₉NO₁₂
• 分子量: 535.505
• InChiKey: JAJWZQXINCTTEN-PRDVQWLOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.15
• 重原子数：
  38.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  173.75
• 氢给体数：
  0.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  [4-(tetra-O-acetyl-β-D-glucopyranosyloxy)-phenyl]-acetic acid 2-cyanoethyl ester 在 偶氮二异丁腈 N-溴代丁二酰亚胺(NBS) 、 TEA 、 sodium carbonate 、 1-羟基苯并三唑 、 silver nitrate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 4,4'-二氨基二苯乙烯-2,2'-二磺酸 、 silver carbonate 作用下， 以 甲醇 、 四氯化碳 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 42.0h， 生成 N-biotinyl-N'-[4-(β-D-glucopyranosyloxy)-phenyl]-fluoroacetyl-3,6-dioxaoctane-1,8-diamine
  参考文献：
  名称：

  Design and Synthesis of Activity Probes for Glycosidases

  摘要：

  [GRAPHICS]A new synthetic route was developed for the preparation of activity probe 1 for beta-glucosidase in this study. The key glycosidation step begins with benzyl p-hydroxyphenylacetate. Benzylic functionalization for the construction of the trapping device was achieved at later stages. Probe 1 was shown to be able to label the target enzyme. This cassette-like design offers great flexibility for future alterations. It would allow the synthetic scheme to expand to other glycosidase probes with different linker/reporter combinations.

  DOI：

  10.1021/ol0265315
• 作为产物：
  描述：

  2,3,4,6-四乙酰氧基-alpha-D-吡喃葡萄糖溴化物 在 palladium on activated charcoal 甲醇 、 4-二甲氨基吡啶 、 氢气 、 silver trifluoromethanesulfonate 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 13.0h， 生成 [4-(tetra-O-acetyl-β-D-glucopyranosyloxy)-phenyl]-acetic acid 2-cyanoethyl ester
  参考文献：
  名称：

  Design and Synthesis of Activity Probes for Glycosidases

  摘要：

  [GRAPHICS]A new synthetic route was developed for the preparation of activity probe 1 for beta-glucosidase in this study. The key glycosidation step begins with benzyl p-hydroxyphenylacetate. Benzylic functionalization for the construction of the trapping device was achieved at later stages. Probe 1 was shown to be able to label the target enzyme. This cassette-like design offers great flexibility for future alterations. It would allow the synthetic scheme to expand to other glycosidase probes with different linker/reporter combinations.

  DOI：

  10.1021/ol0265315

文献信息

• Facile synthesis toward the construction of an activity probe library for glycosidases
  作者：Tong-Hong Shie、Ying-Ling Chiang、Jing-Jer Lin、Yaw-Kuen Li、Lee-Chiang Lo

  DOI：10.1016/j.carres.2005.12.005

  日期：2006.3

  syntheses were performed for the preparation of a library based on the structure of a key intermediate. The recognition head of this library covers a series of six sugars, including alpha- and beta-d-Glc, alpha- and beta-d-Gal, alpha-d-Man, and alpha-l-Fuc. Each member in this versatile intermediate library could serve as the building block in constructing an activity probe for GHs. As demonstrated in this

  已经证明，选择性标记糖苷水解酶（GH）亚家族的化学探针是GH相关研究的有力工具。我们先前已经在模型研究中证明了采用盒式设计的β-葡萄糖苷酶活性探针的设计和合成。在本文中，我们报道了使用（4-羟苯基）乙酸2-氰基乙基酯作为潜伏捕集装置的前体的改进的合成路线。基于关键中间体的结构，进行平行合成以制备文库。该库的识别头涵盖了一系列的六种糖，包括α-和β-d-Glc，α-和β-d-Gal，α-d-Man和α-1-Fuc。这个通用的中间库中的每个成员都可以作为构建GH活性探针的基础。如本研究所示，