(R)-1-((2S,3S,4R,5S)-3,4-diacetoxy-5-(4-nitrophenoxy)tetrahydrofuran-2-yl)ethane-1,2-diyl diacetate | 100645-44-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-1-((2S,3S,4R,5S)-3,4-diacetoxy-5-(4-nitrophenoxy)tetrahydrofuran-2-yl)ethane-1,2-diyl diacetate
• 英文别名: p-nitrophenyl 2,3,5,6-tetra-O-acetyl-β-D-galactofuranoside
• CAS: 100645-44-1
• 化学式: C₂₀H₂₃NO₁₂
• 分子量: 469.402
• InChiKey: QXQLXODSWYVHJM-LCWAXJCOSA-N

物化性质

• 沸点：
  574.5±50.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.06
• 重原子数：
  33.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  166.8
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  (R)-1-((2S,3S,4R,5S)-3,4-diacetoxy-5-(4-nitrophenoxy)tetrahydrofuran-2-yl)ethane-1,2-diyl diacetate 在 α-L-arabinofuranosidase D3 、 sodium methylate 作用下， 以 甲醇 、 acetate buffer 为溶剂， 生成 benzyl β-D-galactofuranosyl-(1->2)-α-D-xylanopyranoside
  参考文献：
  名称：

  An original chemoenzymatic route for the synthesis of β-d-galactofuranosides using an α-l-arabinofuranosidase

  摘要：

  Galactofuranose is a widespread component of cell wall polysaccharides in bacteria, protozoa and fungi, but is totally absent in mammals. Importantly, galactofuranose is a key constituent of major cell envelope polysaccharides in pathogenic mycobacteria. In this respect, galactofaranose-based glycoconjugates are interesting target molecules for drug design. O-Glycosidases and notably beta-D-galactofuranosidases could be useful tools for the chemoenzymatic synthesis of galacto furano sides, but to date no studies of this type have been reported. Here we report the use of a GH 51 alpha-L-arabinofuranosidase for the synthesis Of beta-D-galactofuranosides. We have demonstrated that this enzyme can catalyse both the autocondensation of p-nitrophenyl-beta-D-galactofuranoside and the transgalactofuranosylation of benzyl alpha-D-xylopyranoside, forming p-nitrophenyl beta-D-galactofuranosyl-(1 -> 2)beta-D-galactofuranoside and benzyl beta-D-galactofuranosyl-(1 -> 2)-alpha-D-xylopyranoside, respectively. Both reactions were very regiospecific and the reaction involving benzyl alpha-D-xylopyranoside afforded very high yields (74.8%) of the major product. To our knowledge, this demonstration of chemoenzymatic synthesis of galactofuranosides constitutes the very first use of an O-glycosidase for the synthesis of galactofuranosides. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2005.01.016
• 作为产物：
  描述：

  n-octyl D-galactofuranoside 在 吡啶 、 硫酸 、 三氟化硼乙醚 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 生成 (R)-1-((2S,3S,4R,5S)-3,4-diacetoxy-5-(4-nitrophenoxy)tetrahydrofuran-2-yl)ethane-1,2-diyl diacetate
  参考文献：
  名称：

  An original chemoenzymatic route for the synthesis of β-d-galactofuranosides using an α-l-arabinofuranosidase

  摘要：

  Galactofuranose is a widespread component of cell wall polysaccharides in bacteria, protozoa and fungi, but is totally absent in mammals. Importantly, galactofuranose is a key constituent of major cell envelope polysaccharides in pathogenic mycobacteria. In this respect, galactofaranose-based glycoconjugates are interesting target molecules for drug design. O-Glycosidases and notably beta-D-galactofuranosidases could be useful tools for the chemoenzymatic synthesis of galacto furano sides, but to date no studies of this type have been reported. Here we report the use of a GH 51 alpha-L-arabinofuranosidase for the synthesis Of beta-D-galactofuranosides. We have demonstrated that this enzyme can catalyse both the autocondensation of p-nitrophenyl-beta-D-galactofuranoside and the transgalactofuranosylation of benzyl alpha-D-xylopyranoside, forming p-nitrophenyl beta-D-galactofuranosyl-(1 -> 2)beta-D-galactofuranoside and benzyl beta-D-galactofuranosyl-(1 -> 2)-alpha-D-xylopyranoside, respectively. Both reactions were very regiospecific and the reaction involving benzyl alpha-D-xylopyranoside afforded very high yields (74.8%) of the major product. To our knowledge, this demonstration of chemoenzymatic synthesis of galactofuranosides constitutes the very first use of an O-glycosidase for the synthesis of galactofuranosides. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2005.01.016

文献信息

• Identification and Characterization of a Novel Galactofuranose-Specific β-D-Galactofuranosidase from Streptomyces Species
  作者：Emiko Matsunaga、Yujiro Higuchi、Kazuki Mori、Nao Yairo、Takuji Oka、Saki Shinozuka、Kosuke Tashiro、Minoru Izumi、Satoru Kuhara、Kaoru Takegawa

  DOI：10.1371/journal.pone.0137230

  日期：——

  β-D-galactofuranose (Galf) is a component of polysaccharides and glycoconjugates and its transferase has been well analyzed. However, no β-D-galactofuranosidase (Galf-ase) gene has been identified in any organism. To search for a Galf-ase gene we screened soil samples and discovered a strain, identified as a Streptomyces species by the 16S ribosomal RNA gene analysis, that exhibits Galf-ase activity for 4-nitrophenyl β-D-galactofuranoside (pNP-β-D-Galf) in culture supernatants. By draft genome sequencing of the strain, named JHA19, we found four candidate genes encoding Galf-ases. Using recombinant proteins expressed in Escherichia coli, we found that three out of four candidates displayed the activity of not only Galf-ase but also α-L-arabinofuranosidase (Araf-ase), whereas the other one showed only the Galf-ase activity. This novel Galf-specific hydrolase is encoded by ORF1110 and has an optimum pH of 5.5 and a Km of 4.4 mM for the substrate pNP-β-D-Galf. In addition, this enzyme was able to release galactose residue from galactomannan prepared from the filamentous fungus Aspergillus fumigatus, suggesting that natural polysaccharides could be also substrates. By the BLAST search using the amino acid sequence of ORF1110 Galf-ase, we found that there are homolog genes in both prokaryotes and eukaryotes, indicating that Galf-specific Galf-ases widely exist in microorganisms.

  β-D-半乳糖呋喃糖（Galf）是多糖和糖共轭物的一种成分，其转移酶已被充分分析。然而，目前尚未在任何生物体中发现β-D-半乳糖呋喃糖苷酶（Galf-ase）基因。为了寻找半乳呋喃糖苷酶基因，我们对土壤样本进行了筛选，发现了一株通过 16S 核糖体 RNA 基因分析确定为链霉菌的菌株，该菌株在培养上清液中对 4-硝基苯基 β-D-半乳呋喃糖苷（pNP-β-D-Galf）具有半乳呋喃糖苷酶活性。通过对这株名为 JHA19 的菌株进行基因组测序，我们发现了四个编码 Galf 酶的候选基因。通过在大肠杆菌中表达重组蛋白，我们发现四个候选基因中有三个不仅具有 Galf-酶的活性，而且还具有 α-L-阿拉伯呋喃糖苷酶（Araf-ase）的活性，而另一个则只具有 Galf-酶的活性。这种新型的 Galf 特异性水解酶由 ORF1110 编码，对底物 pNP-β-D-Galf 的最适 pH 值为 5.5，Km 为 4.4 mM。此外，这种酶还能从丝状真菌曲霉制备的半乳甘露聚糖中释放半乳糖残基，这表明天然多糖也可以是底物。通过对ORF1110半乳糖酶的氨基酸序列进行BLAST检索，我们发现原核生物和真核生物中都存在同源基因，这表明微生物中广泛存在半乳糖特异性半乳糖酶。
• Chemo-enzymatic synthesis of p-nitrophenyl β-D-galactofuranosyl disaccharides from Aspergillus sp. fungal-type galactomannan
  作者：Ryo Ota、Yumi Okamoto、Christopher J. Vavricka、Takuji Oka、Emiko Matsunaga、Kaoru Takegawa、Hiromasa Kiyota、Minoru Izumi

  DOI：10.1016/j.carres.2019.01.005

  日期：2019.2

  are important for cell wall integrity. In this study, we investigated the synthesis of p-nitrophenyl β-d-galactofuranoside and its disaccharides by chemo-enzymatic methods including use of galactosidase. The key step was selective removal of the concomitant pyranoside by enzymatic hydrolysis to purify p-nitrophenyl β-d-galactofuranoside, a promising substrate for β-d-galactofuranosidase from Streptomyces

  β-d-半乳糖呋喃糖（加尔夫）是多糖和糖结合物的成分。关于半乳糖呋喃糖基转移酶和半乳糖呋喃糖苷酶（半乳糖苷酶）参与含半乳糖呋喃糖聚糖的合成和降解的报道很少。曲霉属中的丝状真菌的细胞壁包括含半呋喃糖的多糖和糖缀合物，例如O-聚糖，N-聚糖和真菌型半乳甘露聚糖，它们对于细胞壁的完整性很重要。在这项研究中，我们研究了通过化学酶促方法（包括使用半乳糖苷酶）合成对硝基苯基β-d-半乳糖呋喃糖苷及其二糖的方法。关键步骤是通过酶促水解选择性除去伴随的吡喃糖苷，以纯化对硝基苯基β-d-半乳糖呋喃糖苷，