benzimidazol-2-yl 1-thio-α-L-arabinofuranoside | 929006-31-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzimidazol-2-yl 1-thio-α-L-arabinofuranoside
• 英文别名: (2S,3R,4R,5S)-2-(1H-benzimidazol-2-ylsulfanyl)-5-(hydroxymethyl)oxolane-3,4-diol
• CAS: 929006-31-5
• 化学式: C₁₂H₁₄N₂O₄S
• 分子量: 282.32
• InChiKey: VXPMXNDOJKUCNH-MMWGEVLESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  124
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  benzimidazol-2-yl 1-thio-α-L-arabinofuranoside 、 己酸 在 Ruminiclostridium thermocellum arabinofuranosidase 51 E₁₇₃A mutant 、 sodium hydroxide 作用下， 以 aq. phosphate buffer 为溶剂， 反应 16.0h， 以77%的产率得到
  参考文献：
  名称：

  Diversion of a thioglycoligase for the synthesis of 1-O-acyl arabinofuranoses

  摘要：

  来自GH51家族的一种阿拉伯呋喃糖苷水解酶通过突变催化酸/碱氨基酸转变为酰基转移酶。

  DOI：

  10.1039/c8cc01726c
• 作为产物：
  描述：

  1H-苯并咪唑-2-硫醇 在 甲醇 、 三氟化硼乙醚 、 sodium methylate 作用下， 以 二氯甲烷 为溶剂， 生成 benzimidazol-2-yl 1-thio-α-L-arabinofuranoside
  参考文献：
  名称：

  Thioimidoyl furanosides as first inhibitors of the α-l-arabinofuranosidase AbfD3

  摘要：

  Two sets of five thioimidoyl alpha-L-arabino- and beta-D-galactofuranosides were designed, synthesized and subjected to docking studies to evaluate their ability to be recognized by the active site of the alpha-L-arabinofuranosidase AbfD3. Further in vitro assays showed that the targeted furanosides are the first potent inhibitors of this furanosyl hydrolase and that the most efficient one, the thiazolyl alpha-L-arabinofuranoside 1, is a competitive inhibitor having a K-I of 1.4 mu M. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.10.032

文献信息

• Chemo-enzymatic synthesis of an original arabinofuranosyl cluster: optimization of the enzymatic conditions
  作者：Mélanie Almendros、Marc François-Heude、Laurent Legentil、Caroline Nugier-Chauvin、Richard Daniellou、Vincent Ferrières

  DOI：10.3998/ark.5550190.0014.211

  日期：——

  renewable and eco-friendly partner of the glycosylation reaction allowed the one step synthesis of the arabinofuranosyl cluster 4 in 38% yield. Our mutated biocatalyst was able to perform coupling to a multivalent bulky substituent with 80% yield on each arm and pave the way for the further development of enzymatic means of ligation of carbohydrates onto organic scaffolds.

  将突变的糖苷酶评估为糖基化反应的主要、可再生和生态友好伙伴，允许以 38% 的产率一步合成阿拉伯呋喃糖基簇 4。我们的突变生物催化剂能够在每个臂上以 80% 的产率与多价庞大的取代基进行偶联，并为进一步开发将碳水化合物连接到有机支架上的酶促方法铺平了道路。
• Stereoselective Chemoenzymatic Synthesis of UDP-1,2-<i>cis</i>-furanoses from α,β-Furanosyl 1-Phosphates
  作者：Pauline Peltier、Jean-Paul Guégan、Richard Daniellou、Caroline Nugier-Chauvin、Vincent Ferrières

  DOI：10.1002/ejoc.200800742

  日期：2008.12

  broad substrate specificity of this particular enzyme. The chemical synthesis of the needed furanosyl 1-phosphate starting materials was then performed with unprotected thioimidoyl donors. This led to the first stereoselective chemoenzymatic syntheses of UDP-β-L-arabinofuranose, UDP-α-D-fucofuranose and UDP-α-D-6F-galactofuranose from starting mixtures of sugar-phosphates.(© Wiley-VCH Verlag GmbH & Co

  含呋喃糖基的糖缀合物的生物合成描述甚少，主要是由于缺乏 UDP-呋喃糖。在这里，我们展示了我们在多酶系统的帮助下合成稀有核苷酸糖的努力，特别是包括 1-磷酸半乳糖尿苷转移酶。首先，STD-NMR 技术被用来探测这种特定酶的广泛底物特异性。然后用未保护的硫亚氨基供体进行所需的呋喃糖基 1-磷酸起始材料的化学合成。这导致了 UDP-β-L-阿拉伯呋喃糖、UDP-α-D-岩藻呋喃糖和 UDP-α-D-6F-呋喃半乳糖的首次立体选择性化学酶促合成。 （© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
• Exploring the synthetic potency of the first furanothioglycoligase through original remote activation
  作者：Mélanie Almendros、Dantcho Danalev、Marc François-Heude、Pascal Loyer、Laurent Legentil、Caroline Nugier-Chauvin、Richard Daniellou、Vincent Ferrières

  DOI：10.1039/c1ob06227a

  日期：——

  Thioglycosidic bonds are of utmost importance in biomolecules as their incorporation led to more stable glycomimetics with potential drug activities. Until now only chemical methods were available for their incorporation into glycofuranosyl conjugates. Herein, we wish to describe the use of the first furanothioglycoligase for the preparation of a great variety of thioaryl derivatives with moderate to excellent yields. Of great interest, a stable 1-thioimidoyl arabinofuranose, classically used in chemical glycosylation, was able to efficiently act as a donor through an original enzymatic remote activation mechanism. Study of the chemical structure as well as the nucleophilicity of the thiol allowed us to optimize this biocatalyzed process. As a consequence, this mutated enzyme constitutes an original, mild and eco-friendly method of thioligation.

  硫代糖苷键在生物分子中至关重要，因为它们的结合可以产生更稳定的糖模拟物，并具有潜在的药物活性。到目前为止，只有化学方法可将其掺入呋喃糖基缀合物中。在此，我们希望描述第一种呋喃硫代糖连接酶用于以中等至优异的产率制备多种硫代芳基衍生物的用途。令人非常感兴趣的是，传统上用于化学糖基化的稳定的1-硫代亚氨基阿拉伯呋喃糖能够通过原始的酶促远程激活机制有效地充当供体。对硫醇化学结构和亲核性的研究使我们能够优化这种生物催化过程。因此，这种突变酶构成了一种原始、温和且环保的硫连接方法。
• Versatile Synthesis of Rare Nucleotide Furanoses
  作者：Pauline Peltier、Richard Daniellou、Caroline Nugier-Chauvin、Vincent Ferrières

  DOI：10.1021/ol702392x

  日期：2007.12.1

  Direct activation of unprotected thioimidoyl furanosides yielded in only one step and few minutes a panel of rare uridine 5'-diphosphofuranoses. Diastereoselectivity of the reaction was tightly connected with reaction time, temperature, and nature of the furanosyl donor. This approach was totally selective since no ring expansion from the initial five-membered ring to the more stable pyranose form was observed.
• Diversion of a thioglycoligase for the synthesis of 1-<i>O</i>-acyl arabinofuranoses
  作者：Quentin Pavic、Sylvain Tranchimand、Loïc Lemiègre、Laurent Legentil

  DOI：10.1039/c8cc01726c

  日期：——

  An arabinofuranosylhydrolase from the GH51 family was transformed into an acyl transferase by mutation of the catalytic acid/base amino acid.

  来自GH51家族的一种阿拉伯呋喃糖苷水解酶通过突变催化酸/碱氨基酸转变为酰基转移酶。