p-nitrophenyl α-L-arabinofuranosyl-(1->5)-[α-L-arabinofuranosyl-(1->2)]-α-L-arabinofuranoside | 1228460-05-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-nitrophenyl α-L-arabinofuranosyl-(1->5)-[α-L-arabinofuranosyl-(1->2)]-α-L-arabinofuranoside
• 英文别名: Araf(a1-2)[Araf(a1-5)]Araf(a)-O-Ph(4-NO2)；(2R,3R,4R,5S)-2-[[(2S,3S,4R,5S)-4-[(2S,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-3-hydroxy-5-(4-nitrophenoxy)oxolan-2-yl]methoxy]-5-(hydroxymethyl)oxolane-3,4-diol
• CAS: 1228460-05-6
• 化学式: C₂₁H₂₉NO₁₅
• 分子量: 535.459
• InChiKey: LRXZXWCMBZBJJU-JMTUQSDBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.3
• 重原子数：
  37
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  243
• 氢给体数：
  7
• 氢受体数：
  15

反应信息

• 作为产物：
  描述：

  4-硝基苯基-ALPHA-L-阿拉伯糖甙 在 recombinant α-L-arabinofuranosyl hydrolase Araf51 from Clostridium thermocellum 作用下， 反应 0.42h， 以12.6%的产率得到p-nitrophenyl α-L-arabinofuranosyl-(1->2)-α-L-arabinofuranoside
  参考文献：
  名称：

  Enzymatic synthesis of oligo-d-galactofuranosides and l-arabinofuranosides: from molecular dynamics to immunological assays

  摘要：

  含 D-半乳糖呋喃糖基的共轭物在许多病原微生物中无处不在，但在哺乳动物中却完全不存在。由于 D-半乳糖呋喃糖基共轭物可能构成有趣的药食同源物，近期的研究工作致力于制备这种共轭物。除了报道较多的化学方法外，酶解方法仍然有限，主要原因是缺乏相应的生物催化剂。基于化学结构之间的相似性，来自热梭菌的阿拉伯呋喃糖基水解酶 Araf51 预计既能识别 L-Araf 基序，也能识别其 D-Galf 类似物。我们首先利用分子动力学和 STD-NMR 验证了这一假设，并增加了对活性位点的了解。有趣的是，这种阿拉伯呋喃糖苷酶不仅能够水解半乳糖基衍生物，而且在催化以对硝基苯基呋喃糖苷为供体的寡聚反应方面也非常有效。利用质谱和核磁共振测定了所获得产物的结构。在这些产物中，合成了所有可能的二阿拉伯呋喃半乳糖苷和半乳糖呋喃苷的区域异构体，而且每种区域异构体的比例都很容易根据反应时间进行调整。特别是首次用酶法制备了具有生物学相关序列的半乳糖呋喃生物苷β-D-Galf-(1,6)-β-D-Galf。测试了从二-阿拉伯呋喃半乳糖苷到五-阿拉伯呋喃半乳糖苷的所有馏分诱导 TNF-α 生成的能力。在短至三个糖残基的阿拉伯呋喃糖苷中观察到了有趣的免疫特性。

  DOI：

  10.1039/b926988f

文献信息

• Enzymatic synthesis of oligo-d-galactofuranosides and l-arabinofuranosides: from molecular dynamics to immunological assays
  作者：Ilona Chlubnová、Dominik Filipp、Vojtech Spiwok、Hana Dvořáková、Richard Daniellou、Caroline Nugier-Chauvin、Blanka Králová、Vincent Ferrières

  DOI：10.1039/b926988f

  日期：——

  D-Galactofuranosyl-containing conjugates are ubiquitous in many pathogenic microorganisms, but completely absent from mammals. As they may constitute interesting pharmacophores, recent works have been dedicated to their preparation. Besides well-reported chemical procedures, enzymatic approaches are still limited, mainly due to the lack of the corresponding biocatalysts. Based on the similarity between chemical structures, the arabinofuranosyl hydrolase Araf51 from Clostridium thermocellum was expected to recognize both the L-Araf motif and its D-Galf analogue. Molecular dynamics and STD-NMR were firstly used to confirm this hypothesis and increase our knowledge of the active site. Interestingly, this arabinofuranosidase was not only able to hydrolyze galactosyl derivatives, but was also really efficient in catalyzing oligomerisations using p-nitrophenyl furanosides as donors. The structures of the products obtained were determined using mass spectrometry and NMR. Amongst them, all the possible regioisomers of di-arabino and -galactofuranosides were synthesized, and the ratio of each regioisomer was easily tuned with respect to the reaction time. Especially, the galactofuranobioside displaying the biologically relevant sequence β-D-Galf-(1,6)-β-D-Galf was enzymatically prepared for the first time. All fractions going from di- to penta-arabino- and galactofuranosides were tested for their ability in eliciting the production of TNF-α. Interesting immunological properties were observed with arabinofuranosides as short as three sugar residues.

  含 D-半乳糖呋喃糖基的共轭物在许多病原微生物中无处不在，但在哺乳动物中却完全不存在。由于 D-半乳糖呋喃糖基共轭物可能构成有趣的药食同源物，近期的研究工作致力于制备这种共轭物。除了报道较多的化学方法外，酶解方法仍然有限，主要原因是缺乏相应的生物催化剂。基于化学结构之间的相似性，来自热梭菌的阿拉伯呋喃糖基水解酶 Araf51 预计既能识别 L-Araf 基序，也能识别其 D-Galf 类似物。我们首先利用分子动力学和 STD-NMR 验证了这一假设，并增加了对活性位点的了解。有趣的是，这种阿拉伯呋喃糖苷酶不仅能够水解半乳糖基衍生物，而且在催化以对硝基苯基呋喃糖苷为供体的寡聚反应方面也非常有效。利用质谱和核磁共振测定了所获得产物的结构。在这些产物中，合成了所有可能的二阿拉伯呋喃半乳糖苷和半乳糖呋喃苷的区域异构体，而且每种区域异构体的比例都很容易根据反应时间进行调整。特别是首次用酶法制备了具有生物学相关序列的半乳糖呋喃生物苷β-D-Galf-(1,6)-β-D-Galf。测试了从二-阿拉伯呋喃半乳糖苷到五-阿拉伯呋喃半乳糖苷的所有馏分诱导 TNF-α 生成的能力。在短至三个糖残基的阿拉伯呋喃糖苷中观察到了有趣的免疫特性。