p-nitrophenyl 3-deoxy-α-D-ribo-hexopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-nitrophenyl 3-deoxy-α-D-ribo-hexopyranoside
• 英文别名: (2R,3S,5R,6R)-2-(hydroxymethyl)-6-(4-nitrophenoxy)oxane-3,5-diol
• 化学式: C₁₂H₁₅NO₇
• 分子量: 285.254
• InChiKey: WMLPDUAEJYTELC-QCNOEVLYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  125
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl 1-thio-β-D-glucopyranoside 、 p-nitrophenyl 3-deoxy-α-D-ribo-hexopyranoside 在 sodium acetate buffer 、 Aspergillus niger α-glucosidase 作用下， 以 乙腈 为溶剂， 反应 12.0h， 生成 ethyl 3-deoxy-α-D-ribo-hexopyranosyl-(1->6)-β-D-thioglucopyranoside
  参考文献：
  名称：

  Glycosidase-catalyzed Deoxy Oligosaccharide Synthesis. Practical Synthesis of Monodeoxy Analogs of Ethyl β-Thioisomaltoside UsingAspergillus nigerα-Glucosidase

  摘要：

  使用对硝基苯α-D-吡喃葡萄糖苷（Glcα-O-pNP）的四种可能的单脱氧类似物（分别在 C-2、C-3、C-4 和 C-6 位置进行修饰）（2D-、3D-、4D- 和 6D-Glcα-O-pNP）作为糖基供体，以及六种等量的乙基β-D-硫代吡喃葡萄糖苷（Glcβ-S-Et）作为糖基受体，进行酶促转糖基化、分别）作为糖基供体，六当量的乙基 β-D-硫代吡喃葡萄糖苷（Glcβ-S-Et）作为糖基受体，生成葡萄糖寡糖的单脱氧衍生物。该反应是在 50 mM 醋酸钠缓冲液（pH 4.0）/CH3CN（1: 1 v/v）的混合物中，于 37°C 下使用纯化的黑曲霉 α-葡萄糖苷酶催化的。在 2D-Glcα-O-pNP 和 Glcβ-S-Et 的反应中观察到该酶的高活性，从而得到乙基 β-硫代异麦芽糖苷和乙基 β-硫代异麦芽糖苷的单脱氧类似物、即乙基 2-脱氧-α-D-阿拉伯-六吡喃糖基-(1,4)-β-D-硫代吡喃葡萄糖苷和乙基 2-脱氧-α-D-阿拉伯-六吡喃糖基-(1,6)-β-D-硫代吡喃葡萄糖苷，分离率分别为 6.72% 和 46.6% 的分离收率（基于 2D-Glcα-O-pNP ）。此外，从三维-Glcα-O-pNP 和 Glcβ-S-Et 中，该酶还催化合成了乙基 β-硫代异麦芽糖苷的 3-脱氧类似物，即乙基 3-脱氧-α-D-核糖基-己吡喃糖基-(1,6)-β-D-硫代吡喃葡萄糖苷，分离产率为 23.0%（基于三维-Glcα-O-pNP）。4D- 或 6D-Glcα-O-pNP 与 Glcβ-S-Et 的酶促反应没有得到产物。

  DOI：

  10.1271/bbb.67.1024

文献信息

• Glycon specificity profiling of α-glucosidases using monodeoxy and mono-O-methyl derivatives of p-nitrophenyl α-d-glucopyranoside
  作者：Toshiyuki Nishio、Wataru Hakamata、Atsuo Kimura、Seiya Chiba、Akira Takatsuki、Ryu Kawachi、Tadatake Oku

  DOI：10.1016/s0008-6215(02)00026-5

  日期：2002.4

  Hydrolysis of probe substrates, eight possible monodeoxy and mono-O-methyl analogs of p-nitrophenyl alpha-D-glucopyranoside (pNP alpha-D-Glc). modified at the C-2, C-3, C-4. and C-6 positions. was studied as part of investigations into the glycon specificities of seven alpha-glucosidases (EC 3.2.1.20) isolated from Saccharomyces cerevisiae, Bacillus stearothermophilus, honeybee (two enzymes). sugar beet, flint corn, and Aspergillus niger. The glucosidases from sugar beet, flint corn. and A. niger were found to hydrolyze the 2-deoxy analogs with substantially higher activities than against pNP alpha-D-Glc. Moreover, the flint corn and A. niger enzymes showed hydrolyzing activities, although low, for the 3-deoxy analog. The other four alpha-glucosidases did not exhibit any activities for either the 2- or the 3-deoxy analogs. None of the seven enzymes exhibited any activities toward the 4-deoxy, 6-deoxy, or any of the methoxy analogs. The hydrolysis results, with the deoxy substrate analogs, demonstrated that alpha-glucosidases having remarkably different glycon specificities exist in nature. Further insight into the hydrolysis of deoxyglycosides was obtained by determining the kinetic parameters (k(cat) and K-m) for the reactions of sugar beet, flint corn, and A. niger enzymes. (C) 2002 Elsevier Science Ltd. All rights reserved.