2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl bromide | 42868-96-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl bromide
• 英文别名: 2,3,5-Tri-O-benzoyl-alpha-L-arabinofuranosyl bromide；[(2S,3S,4R,5S)-3,4-dibenzoyloxy-5-bromooxolan-2-yl]methyl benzoate
• CAS: 42868-96-2
• 化学式: C₂₆H₂₁BrO₇
• 分子量: 525.353
• InChiKey: JRRCGOOKGUSEFK-MYDTUXCISA-N

物化性质

• 沸点：
  611.4±55.0 °C(Predicted)
• 密度：
  1.49±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  88.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl bromide 在 甲醇 、 无水碳酸镉 、 氨 作用下， 以 硝基甲烷 为溶剂， 反应 24.17h， 生成 2-((2S,3R,4R,5S)-3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-9-hydroxy-5,11-dimethyl-6H-pyrido[4,3-b]carbazol-2-ium; bromide
  参考文献：
  名称：

  Synthesis and antitumor activity of quaternary ellipticine glycosides, a series of novel and highly active antitumor agents

  摘要：

  A series of ellipticine glycosides [2-N-glycosyl quaternary pyridinium salts of three ellipticines: ellipticine (1), 9-methoxyellipticine (2), and 9-hydroxyellipticine (4)] were stereoselectively synthesized in good yields by an improved condensation reaction between ellipticines [1, 2, and 9-acetoxyellipticine (3)] and protected (peracylated and perbenzylated) glycosyl halides with cadmium carbonate, followed by deprotection. These glycosides were preliminarily evaluated for their antitumor activity in the L1210 leukemia system. Twenty-six (53%) of the 49 glycosides tested were curative, and five [9-hydroxyellipticine L-arabinopyranoside (41b), D-lyxofuranoside (43a), L-lyxopyranoside (44b), D-xylofuranoside (49a), and L-rhamnopyranoside (56)] were selected for extended evaluation on the basis of their high levels of activity. The structure-activity relationships are discussed. The selected glycosides showed remarkable activity in six different murine tumor systems with excellent therapeutic ratios; their efficacy surpassed that of doxorubicin against three of these systems. On the basis of these results and ease of formulation, the two glycosides 41b (SUN4599) and 49a (SUN5073) were selected for further preclinical evaluation and possible clinical development.

  DOI：

  10.1021/jm00402a007
• 作为产物：
  描述：

  L-阿拉伯糖 在 吡啶 、 盐酸 、 硫酸 、 氢溴酸 、 溶剂黄146 、 乙酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 62.0h， 生成 2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl bromide
  参考文献：
  名称：

  具有改善的转糖基化活性的Araf51：一种针对一种特定受体的工程化生物催化剂

  摘要：

  为了获得用于合成烷基阿拉伯呋喃糖苷的有效生物催化剂，已经进行了阿拉伯呋喃呋喃糖基水解酶Araf51的随机诱变。选择突变体是基于其催化用作供体的对硝基苯基α-L-阿拉伯呋喃糖苷（pNP-Araf）和各种脂族醇作为受体的转糖基化反应的能力。这种筛选策略强调了5个有趣的克隆，每个克隆对应一个受体。与野生型酶相比，它们在转糖基化反应中似乎更有效，而未检测到自缩合或水解产物。此外，突变体对已为其选择了醇的高特异性证实了筛选过程。突变酶的序列分析表明，

  DOI：

  10.1016/j.carres.2014.10.031

文献信息

• Active-site-directed irreversible inhibition of glycosidases by the corresponding glycosylmethyl-(p-nitrophenyl)triazenes
  作者：Philip J. Marshall、Michael L. Sinnott、Paul J. Smith、Danny Widdows

  DOI：10.1039/p19810000366

  日期：——

  β-D-Galactopyranosylmethyl-(p-nitrophenyl)triazene is an active-site-directed irreversible inhibitor (ASDIN) of the ebg° and the lacZβ-galactosidases of Escherichia coli, of the β-galactosidase of human-liver lysosomes, and, less effectively, of the α-galactosidase of green coffee beans; it has no effect on the lac repressor of E. coli. β-D-Glucopyranosylmethyl-(p-nitrophenyl)triazene is an ASDIN of both β-glucosidase

  β- d -Galactopyranosylmethyl-（p硝基苯基）三氮烯是有源的位点定向的不可逆抑制剂的的（ASDIN）EBG °和lacZ启动的β半乳糖苷酶的大肠杆菌人类肝溶酶体的β半乳糖苷酶的，和，效果较差的生咖啡豆的α-半乳糖苷酶；它对大肠杆菌的lac阻遏物没有影响。β- D-葡糖基糖基甲基-（对硝基苯基）三氮烯是甜杏仁β-葡糖苷酶B的β-葡糖苷酶和β-半乳糖苷酶活性的ASDIN。对大肠杆菌的酵母α-葡萄糖苷酶，lacZβ-半乳糖苷酶没有影响或黑曲霉（Aspergillus niger）的葡糖淀粉酶。β- D-木吡喃糖基甲基-（对硝基苯基）三氮烯是来自沃特曼青霉的β-木糖苷酶的ASDIN ，但对短小芽孢杆菌的β-木糖苷酶没有影响，但由于其消耗了稳定的二硫苏糖醇。α - L-阿拉伯呋喃糖基甲基-（对硝基苯基）三氮烯是甜叶念珠菌胞外α- L-阿拉伯呋喃糖苷酶的ASDIN在pH为7时
• Active Site Mapping of Xylan-Deconstructing Enzymes with Arabinoxylan Oligosaccharides Produced by Automated Glycan Assembly
  作者：Deborah Senf、Colin Ruprecht、Goswinus H. M. de Kruijff、Sebastian O. Simonetti、Frank Schuhmacher、Peter H. Seeberger、Fabian Pfrengle

  DOI：10.1002/chem.201605902

  日期：2017.3.2

  as the production of biofuel. To determine the substrate specificities of these enzymes, we prepared a collection of complex xylan oligosaccharides by automated glycan assembly. Seven differentially protected building blocks provided the basis for the modular assembly of 2‐substituted, 3‐substituted, and 2‐/3‐substituted arabino‐ and glucuronoxylan oligosaccharides. Elongation of the xylan backbone

  木聚糖降解酶对于半纤维素生物质的解构至关重要，因此水解产物可用于各种工业应用，例如生物燃料的生产。为了确定这些酶的底物特异性，我们通过自动聚糖组装制备了复杂的木聚糖寡糖集合。七个差异保护的构建基块为2取代，3取代和2/3取代的阿拉伯糖醛酸和葡萄糖醛酸木聚糖低聚糖的模块化组装提供了基础。木聚糖主链的延长取决于将C4-芴基甲氧基羰基（Fmoc）保护的木糖结构单元反复添加到接头官能化的树脂中。阿拉伯呋喃糖和葡萄糖醛酸残基已通过在木糖结构单元的C2和C3羟基上使用完全正交的2-（甲基）萘基（Nap）和2-（叠氮基甲基）苯甲酰基（Azmb）保护基团选择性地连接至主链。阿拉伯木聚糖低聚糖是绘制涉及木聚糖解构的糖基水解酶活性位点的极佳工具。在寡糖与糖基水解酶孵育后，通过分析消化产物来确定几种木聚糖酶和阿拉伯呋喃糖苷酶的底物特异性。
• Preparation and conformation of α-l-arabinofuranosyl-pyridinium salts, and hydrolysis of the 4-bromoisoquinolinium compound
  作者：Michael L. Sinnott、W.S.Sulochana Wijesundera

  DOI：10.1016/0008-6215(85)85209-5

  日期：1985.2

  -benzoyl-α- l -arabinofuranosylpyridinium salts can be made inacceptable yields and high stereochemical purity by the reaction of 2,3,5-tri- O -benzoyl-α- l -arabinofuranosyl bromide and the pyridine in the presence of tetrabutylammonium bromide. Analysis of the 1 H-n.m.r. signals of the sugar reveals that the benzoylated compounds adopt largely the E 2 conformation whereas the debenzoylated compounds are

  摘要在存在条件下，通过2,3,5-三-O-苯甲酰基-α-1-阿拉伯呋喃糖基溴化物与吡啶的反应，可以使三邻-苯甲酰基-α-1-阿拉伯呋喃糖基吡啶鎓盐的收率和立体化学纯度高。四丁基溴化铵。糖的1 Hn.mr信号分析表明，苯甲酰化化合物主要采用E 2构象，而脱苯甲酰化化合物主要采用o T 1构象。α-1-阿拉伯呋喃糖基-4-溴异喹啉鎓离子通过非pH依赖性途径和碱催化途径水解，并在碱中可逆地形成惰性假碱。就呋喃糖苷的酸稳定性而言，讨论了pH依赖性反应的相对较低的速率。
• Alpha-L-arabinofuranosidase histochemical reporter gene assay
  申请人：Sauer L. Brian

  公开号：US20060094031A1

  公开（公告）日：2006-05-04

  The present invention provides a novel reporter gene assay. In particular, the present invention provides a histochemical reporter gene assay employing α- L -arabinofuranosidase in combination with a chromogenic α- L -arabinofuranosidase substrate. The α- L -arabinofuranosidase histochemical reporter assay may be utilized to characterize gene regulatory regions of interest either alone or in combination with other assays.

  本发明提供了一种新型的报告基因测定法。特别地，本发明提供了一种利用α-L-阿拉比诺糖苷酶与色原性α-L-阿拉比诺糖苷酶底物结合的组织化学报告基因测定法。α-L-阿拉比诺糖苷酶组织化学报告测定法可用于单独或与其他测定法结合使用，以表征感兴趣的基因调控区域。
• Synthesis of trisaccharides related to an arabinoglucan
  作者：Tadami Fujiwara、Tadahiro Takeda、Yukio Ogihara

  DOI：10.1016/s0008-6215(00)90767-5

  日期：1985.8

  Synthese de l'O-α-L-arabinofuranosyl-6 O-α-D-glucopyranosyl-4 β-D-glucopyranoside de methyle et de l'O-[O-α-L-arabinofuranosyl-6 β-D-glucopyranosyl]-4 β-D-glucopyranoside de methyle

  合成l'O-α-L-阿拉伯呋喃糖基-6O-α-D-吡喃葡萄糖基-4β-D-吡喃葡萄糖苷甲基和de'O- [O-α-L-阿拉伯呋喃糖基-6β-D-吡喃葡萄糖基] -4β-D-吡喃葡萄糖苷甲基