2-naphthyl 2-deoxy-2-fluoro-β-D-xylopyranoside | 1315279-36-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-naphthyl 2-deoxy-2-fluoro-β-D-xylopyranoside
• 英文别名: (3R,4S,5R,6S)-5-fluoro-6-naphthalen-2-yloxyoxane-3,4-diol
• CAS: 1315279-36-7
• 化学式: C₁₅H₁₅FO₄
• 分子量: 278.28
• InChiKey: OHGPLYBZYJGMGE-KBXIAJHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-naphthyl 2-deoxy-2-fluoro-β-D-xylopyranoside 在 四丁基硫酸氢铵 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 sodium hydroxide 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 48.0h， 生成
  参考文献：
  名称：

  双修饰木糖苷类似物的合成以探测β4GalT7活性位点

  摘要：

  已经显示单取代的萘氧基氯化物作为酶β4GalT7的底物和抑制剂，β4GalT7是导致糖胺聚糖和蛋白聚糖的生物合成途径中的关键酶。在本文中，我们探索了在两个不同位置修饰的16种木糖苷类似物的合成，以及它们作为酶的抑制剂和/或底物的功能。看来简单的化合物需要复杂的合成途径。对合成工作的荟萃分析表明，不管碳水化合物合成方法的丰富性如何，即使简单的修饰也可能是有问题的，而双重修饰由于构象，空间和立体电子效应而带来了其他挑战。

  DOI：

  10.1021/acs.joc.7b02809
• 作为产物：
  描述：

  (1R,3S,4S,6R,9S,10R)-10-hydroxy-3,4-dimethoxy-3,4-dimethyl-9-(2-naphthyl)oxy-2,5,8-trioxabicyclo[4.4.0]decane 在 吡啶 、 二乙胺基三氟化硫 、 sodium methylate 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 78.75h， 生成 2-naphthyl 2-deoxy-2-fluoro-β-D-xylopyranoside
  参考文献：
  名称：

  Synthesis, conformation and biology of naphthoxylosides

  摘要：

  Proteoglycans (PG) are polyanionic proteins consisting of a core protein substituted with carbohydrate chains, that is, glycosaminoglycans (GAG). The biosynthesis of GAG can be manipulated by simple xylosides carrying hydrophobic aglycons, which can enter the cell and initiate the biosynthesis. While the importance of the aglycon is well investigated, there is far less information on the effect of modifications in the xylose residue.We have developed a new synthetic protocol, based on acetal protection and selective benzylation, for modification of the three hydroxyl groups in xylose. Thus we have synthesized twelve analogs of 2-naphthyl beta-D-xylopyranoside (XylNap), where each hydroxyl group has been epimerized or replaced by methoxy, fluoro, or hydrogen.To gain more information about the properties of xylose, conformational studies were made on some of the analogs. It was found that the (4)C(1) conformation is highly predominant, accompanied by a nonnegligible population of the (2)S(0) conformation. However, deoxygenation at C3 results in a large portion of the (1)C(4) conformation.The GAG priming ability and proliferation activity of the twelve analogs, were investigated using a matched pair of human breast fibroblasts and human breast carcinoma cells. None of the analogs initiated the biosynthesis of GAG, but an inhibitory effect on endogenous PG production was observed for analogs fluorinated or deoxygenated at C4. From our data it seems reasonable that all three hydroxyl groups in XylNap are essential for the priming of GAG chains and for selective toxicity for tumor cells. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.05.007

文献信息

• Synthesis, conformation and biology of naphthoxylosides
  作者：Anna Siegbahn、Ulrika Aili、Agata Ochocinska、Martin Olofsson、Jerk Rönnols、Katrin Mani、Göran Widmalm、Ulf Ellervik

  DOI：10.1016/j.bmc.2011.05.007

  日期：2011.7

  Proteoglycans (PG) are polyanionic proteins consisting of a core protein substituted with carbohydrate chains, that is, glycosaminoglycans (GAG). The biosynthesis of GAG can be manipulated by simple xylosides carrying hydrophobic aglycons, which can enter the cell and initiate the biosynthesis. While the importance of the aglycon is well investigated, there is far less information on the effect of modifications in the xylose residue.We have developed a new synthetic protocol, based on acetal protection and selective benzylation, for modification of the three hydroxyl groups in xylose. Thus we have synthesized twelve analogs of 2-naphthyl beta-D-xylopyranoside (XylNap), where each hydroxyl group has been epimerized or replaced by methoxy, fluoro, or hydrogen.To gain more information about the properties of xylose, conformational studies were made on some of the analogs. It was found that the (4)C(1) conformation is highly predominant, accompanied by a nonnegligible population of the (2)S(0) conformation. However, deoxygenation at C3 results in a large portion of the (1)C(4) conformation.The GAG priming ability and proliferation activity of the twelve analogs, were investigated using a matched pair of human breast fibroblasts and human breast carcinoma cells. None of the analogs initiated the biosynthesis of GAG, but an inhibitory effect on endogenous PG production was observed for analogs fluorinated or deoxygenated at C4. From our data it seems reasonable that all three hydroxyl groups in XylNap are essential for the priming of GAG chains and for selective toxicity for tumor cells. (C) 2011 Elsevier Ltd. All rights reserved.
• Synthesis of Double-Modified Xyloside Analogues for Probing the β4GalT7 Active Site
  作者：Daniel Willén、Dennis Bengtsson、Sebastian Clementson、Emil Tykesson、Sophie Manner、Ulf Ellervik

  DOI：10.1021/acs.joc.7b02809

  日期：2018.2.2

  article, we explore the synthesis of 16 xyloside analogues, modified at two different positions, as well as their function as inhibitors of and/or substrates for the enzyme. Seemingly simple compounds turned out to require complex synthetic pathways. A meta-analysis of the synthetic work shows that, regardless of the abundance of methods available for carbohydrate synthesis, even simple modifications

  已经显示单取代的萘氧基氯化物作为酶β4GalT7的底物和抑制剂，β4GalT7是导致糖胺聚糖和蛋白聚糖的生物合成途径中的关键酶。在本文中，我们探索了在两个不同位置修饰的16种木糖苷类似物的合成，以及它们作为酶的抑制剂和/或底物的功能。看来简单的化合物需要复杂的合成途径。对合成工作的荟萃分析表明，不管碳水化合物合成方法的丰富性如何，即使简单的修饰也可能是有问题的，而双重修饰由于构象，空间和立体电子效应而带来了其他挑战。