2-propyl β-D-fucopyranoside | 1283768-43-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-propyl β-D-fucopyranoside
• 英文别名: (2R,3R,4S,5R,6R)-2-methyl-6-propan-2-yloxyoxane-3,4,5-triol
• CAS: 1283768-43-3
• 化学式: C₉H₁₈O₅
• 分子量: 206.239
• InChiKey: RQZRUQFNUZLSPX-QMGXLNLGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  79.2
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-硝基苯-BETA-D-吡喃半乳糖苷 、 异丙醇 在 recombinant β-D-galactosidase from Paenibacillus thiaminolyticus, histidine-tagged protein 作用下， 反应 4.0h， 以24%的产率得到2-propyl β-D-fucopyranoside
  参考文献：
  名称：

   -D-Galactosidase from Paenibacillus thiaminolyticus catalyzing transfucosylation reactions

  摘要：

  构建了细菌株Paenibacillus thiaminolyticus的基因组文库，并对克隆中包含编码具有β-d-岩藻糖苷酶活性的β-d-半乳糖苷酶基因的质粒DNA进行了测序。采用大肠杆菌BL21（DE3）细胞生产该酶，形式为带有组氨酸标签的蛋白质。使用Ni-NTA琼脂糖亲和层析纯化了该重组融合蛋白，并通过使用对硝基苯基β-d-岩藻糖吡喃苷（Km值为(1.18 ± 0.06) mmol/L）、对硝基苯基β-d-半乳糖吡喃苷（Km值为(250 ± 40) mmol/L）、对硝基苯基β-d-葡萄糖吡喃苷（Km值为(77 ± 6) mmol/L）和乳糖（Km值为(206 ± 5) mmol/L）作为底物进行特征分析。最佳pH和温度分别估计为5.5和65°C。根据氨基酸序列计算，该融合蛋白的分子量为68.6 kDa，凝胶过滤层析确认该酶以单体形式存在。在接下来的步骤中，测试其催化转岩藻糖化反应的能力。该酶能够催化将岩藻糖基转移到不同的对硝基苯基糖吡喃苷上（生成对硝基苯基β-d-岩藻糖苷-(1,3)-β-d-岩藻糖苷、对硝基苯基β-d-岩藻糖苷-(1,3)-α-d-葡萄糖苷、对硝基苯基β-d-岩藻糖苷-(1,3)-α-d-甘露糖苷和对硝基苯基β-d-岩藻糖苷-(1,6)-α-d-半乳糖苷）和醇类（生成甲基β-d-岩藻糖苷、乙基β-d-岩藻糖苷、1-丙基β-d-岩藻糖苷、2-丙基β-d-岩藻糖苷、1-辛基β-d-岩藻糖苷和2-辛基β-d-岩藻糖苷）。这些结果表明使用该酶作为酶促合成β-d-岩藻糖化分子的有希望工具的可能性。

  DOI：

  10.1093/glycob/cwp196

文献信息

•  -D-Galactosidase from Paenibacillus thiaminolyticus catalyzing transfucosylation reactions
  作者：E. Benesova、P. Lipovova、H. Dvorakova、B. Kralova

  DOI：10.1093/glycob/cwp196

  日期：2010.4.1

  A genomic library of bacterial strain Paenibacillus thiaminolyticus was constructed and the plasmid DNA of the clone, containing the gene encoding β-d-galactosidase with β-d-fucosidase activity, detected by 5-bromo-4-chloro-3-indoxyl β-d-galactopyranoside, was sequenced. Cells of Escherichia coli BL21 (DE3) were used for production of the enzyme in the form of a histidine-tagged protein. This recombinant fusion protein was purified using Ni-NTA agarose affinity chromatography and characterized by using p-nitrophenyl β-d-fucopyranoside (Km value of (1.18 ± 0.06) mmol/L), p-nitrophenyl β-d-galactopyranoside (Km value of (250 ± 40) mmol/L), p-nitrophenyl β-d-glucopyranoside (Km value of (77 ± 6) mmol/L), and lactose (Km value of (206 ± 5) mmol/L) as substrates. Optimal pH and temperature were estimated as 5.5 and 65°C, respectively. According to the amino acid sequence, the molecular weight of the fusion protein was calculated to be 68.6 kDa and gel filtration chromatography confirmed the presence of the enzyme in a monomeric form. In the following step, its ability to catalyze transfucosylation reactions was tested. The enzyme was able to catalyze the transfer of fucosyl moiety to different p-nitrophenyl glycopyranosides (producing p-nitrophenyl β-d-fucopyranosyl-(1,3)-β-d-fucopyranoside, p-nitrophenyl β-d-fucopyranosyl-(1,3)-α-d-glucopyranoside, p-nitrophenyl β-d-fucopyranosyl-(1,3)-α-d-mannopyranoside, and p-nitrophenyl β-d-fucopyranosyl-(1,6)-α-d-galactopyranoside) and alcohols (producing methyl β-d-fucopyranoside, ethyl β-d-fucopyranoside, 1-propyl β-d-fucopyranoside, 2-propyl β-d-fucopyranoside, 1-octyl β-d-fucopyranoside, and 2-octyl β-d-fucopyranoside). These results indicate the possibility of utilizing this enzyme as a promising tool for enzymatic synthesis of β-d-fucosylated molecules.

  构建了细菌株Paenibacillus thiaminolyticus的基因组文库，并对克隆中包含编码具有β-d-岩藻糖苷酶活性的β-d-半乳糖苷酶基因的质粒DNA进行了测序。采用大肠杆菌BL21（DE3）细胞生产该酶，形式为带有组氨酸标签的蛋白质。使用Ni-NTA琼脂糖亲和层析纯化了该重组融合蛋白，并通过使用对硝基苯基β-d-岩藻糖吡喃苷（Km值为(1.18 ± 0.06) mmol/L）、对硝基苯基β-d-半乳糖吡喃苷（Km值为(250 ± 40) mmol/L）、对硝基苯基β-d-葡萄糖吡喃苷（Km值为(77 ± 6) mmol/L）和乳糖（Km值为(206 ± 5) mmol/L）作为底物进行特征分析。最佳pH和温度分别估计为5.5和65°C。根据氨基酸序列计算，该融合蛋白的分子量为68.6 kDa，凝胶过滤层析确认该酶以单体形式存在。在接下来的步骤中，测试其催化转岩藻糖化反应的能力。该酶能够催化将岩藻糖基转移到不同的对硝基苯基糖吡喃苷上（生成对硝基苯基β-d-岩藻糖苷-(1,3)-β-d-岩藻糖苷、对硝基苯基β-d-岩藻糖苷-(1,3)-α-d-葡萄糖苷、对硝基苯基β-d-岩藻糖苷-(1,3)-α-d-甘露糖苷和对硝基苯基β-d-岩藻糖苷-(1,6)-α-d-半乳糖苷）和醇类（生成甲基β-d-岩藻糖苷、乙基β-d-岩藻糖苷、1-丙基β-d-岩藻糖苷、2-丙基β-d-岩藻糖苷、1-辛基β-d-岩藻糖苷和2-辛基β-d-岩藻糖苷）。这些结果表明使用该酶作为酶促合成β-d-岩藻糖化分子的有希望工具的可能性。