allyl 2,4-di-O-benzoyl-α-D-mannopyranoside | 314038-22-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 2,4-di-O-benzoyl-α-D-mannopyranoside
• 英文别名: [(2R,3S,4S,5S,6S)-5-benzoyloxy-4-hydroxy-2-(hydroxymethyl)-6-prop-2-enoxyoxan-3-yl] benzoate
• CAS: 314038-22-7
• 化学式: C₂₃H₂₄O₈
• 分子量: 428.439
• InChiKey: XCLYEDHYIOOSSL-SWMXPCKBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  31
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  allyl 2,4-di-O-benzoyl-α-D-mannopyranoside 在 四(三苯基膦)钯 、 三氟甲磺酸三甲基硅酯 、 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl-(1->3)-[2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl-(1->6)-]-2,4-di-O-benzoyl-α-D-mannopyranosyl trichloroacetimidate
  参考文献：
  名称：

  Identification of trimannoside-recognizing peptide sequences from a T7 phage display screen using a QCM device

  摘要：

  Here, we report on the identification of trimannoside-recognizing peptide sequences from a T7 phage display screen using a quartz-crystal microbalance (QCM) device. A trimannoside derivative that can form a self-assembled monolayer (SAM) was synthesized and used for immobilization on the gold electrode surface of a QCM sensor chip. After six sets of one-cycle affinity selection, T7 phage particles displaying PSVGLFTH (8-mer) and SVGLGLGFSTVNCF (14-mer) were found to be enriched at a rate of 17/44, 9/44, respectively, suggesting that these peptides specifically recognize trimannoside. Binding checks using the respective single T7 phage and synthetic peptide also confirmed the specific binding of these sequences to the trimannoside-SAM. Subsequent analysis revealed that these sequences correspond to part of the primary amino acid sequence found in many mannose- or hexose- related proteins. Taken together, these results demonstrate the effectiveness of our T7 phage display environment for affinity selection of binding peptides. We anticipate this screening result will also be extremely useful in the development of inhibitors or drug delivery systems targeting polysaccharides as well as further investigations into the function of carbohydrates in vivo. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.11.004
• 作为产物：
  描述：

  allyl 6-O-trityl-α-D-mannopyranoside 在 吡啶 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 allyl 2,4-di-O-benzoyl-α-D-mannopyranoside
  参考文献：
  名称：

  高效和实用的N聚糖对应的三种五糖核心结构的合成

  摘要：

  有效地合成了三种支链五糖衍生物和一种四糖。该方法的优点包括一锅轻松合成3,6-差异保护的甘露糖结构单元和有效的寡糖组装策略。

  DOI：

  10.1016/s0040-4020(00)01161-3

文献信息

• Highly Efficient and Practical Synthesis of 3,6-Branched Oligosaccharides
  作者：Yuguo Du、Meimei Zhang、Fanzuo Kong

  DOI：10.1021/ol000243w

  日期：2000.11.1

  [reaction: see text] A one-pot formation of the 3- and 6-OH differentially protected sugar synthon was described. A mannopyranosyl pentasaccharide and a glucopyranosyl hexasaccharide were prepared employing this new finding.

  [反应：见正文]描述了3-锅和6-OH差异保护的糖合成子的一锅形成。利用这一新发现制备了甘露吡喃糖基五糖和葡糖吡喃糖基六糖。
• Radical halogenation-mediated latent–active glycosylations of allyl glycosides
  作者：Rita Pal、Anupama Das、Narayanaswamy Jayaraman

  DOI：10.1039/c7cc07332a

  日期：——

  Radical halogenation-mediated glycosylation using allyl glycosides as donors and as acceptors emerges to be an efficient and hither-to unknown glycosylation method, adhering to the concept of the latent–active methodology. Several di- and trisaccharides that possess the allyl moiety at their reducing end are prepared through this new glycosylation methodology.

  使用烯丙基糖苷作为供体和受体的自由基卤代介导的糖基化方法是一种有效且迄今未知的糖基化方法，它秉承了潜伏性-活性方法学的概念。通过这种新的糖基化方法制备了几种在其还原端具有烯丙基部分的二糖和三糖。
• Identification of trimannoside-recognizing peptide sequences from a T7 phage display screen using a QCM device
  作者：Kazusa Nishiyama、Yoichi Takakusagi、Tomoe Kusayanagi、Yuki Matsumoto、Shiori Habu、Kouji Kuramochi、Fumio Sugawara、Kengo Sakaguchi、Hideyo Takahashi、Hideaki Natsugari、Susumu Kobayashi

  DOI：10.1016/j.bmc.2008.11.004

  日期：2009.1

  Here, we report on the identification of trimannoside-recognizing peptide sequences from a T7 phage display screen using a quartz-crystal microbalance (QCM) device. A trimannoside derivative that can form a self-assembled monolayer (SAM) was synthesized and used for immobilization on the gold electrode surface of a QCM sensor chip. After six sets of one-cycle affinity selection, T7 phage particles displaying PSVGLFTH (8-mer) and SVGLGLGFSTVNCF (14-mer) were found to be enriched at a rate of 17/44, 9/44, respectively, suggesting that these peptides specifically recognize trimannoside. Binding checks using the respective single T7 phage and synthetic peptide also confirmed the specific binding of these sequences to the trimannoside-SAM. Subsequent analysis revealed that these sequences correspond to part of the primary amino acid sequence found in many mannose- or hexose- related proteins. Taken together, these results demonstrate the effectiveness of our T7 phage display environment for affinity selection of binding peptides. We anticipate this screening result will also be extremely useful in the development of inhibitors or drug delivery systems targeting polysaccharides as well as further investigations into the function of carbohydrates in vivo. (c) 2008 Elsevier Ltd. All rights reserved.
• Efficient and practical syntheses of three pentasaccharides core structures corresponding to N -glycans
  作者：Yuguo Du、Meimei Zhang、Fanzuo Kong

  DOI：10.1016/s0040-4020(00)01161-3

  日期：2001.2

  Three branched pentasaccharide derivatives and one tetrasaccharide were synthesized efficiently. The advantages of this method include a one-pot facile synthesis of 3,6-differentially protected mannose building block and an efficient strategy for oligosaccharide assembly.

  有效地合成了三种支链五糖衍生物和一种四糖。该方法的优点包括一锅轻松合成3,6-差异保护的甘露糖结构单元和有效的寡糖组装策略。