2-naphthyl 3-deoxy-β-D-erythropyranoside | 1315279-48-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-naphthyl 3-deoxy-β-D-erythropyranoside
• 英文别名: (2S,3R,5S)-2-naphthalen-2-yloxyoxane-3,5-diol
• CAS: 1315279-48-1
• 化学式: C₁₅H₁₆O₄
• 分子量: 260.29
• InChiKey: RLZPVXPMVATHFL-CFVMTHIKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 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：
  4

反应信息

• 作为反应物：
  描述：

  2-naphthyl 3-deoxy-β-D-erythropyranoside 在 偶氮二异丁腈 、 次磷酸 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 以 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.67h， 生成 (2S,5S)-5-hydroxy-2-(2-naphthyloxy)oxane
  参考文献：
  名称：

  羟基氧烷作为木糖苷类似物，用于确定β4GalT7的最低结合要求

  摘要：

  β-1,4-半乳糖基转移酶7（β4GalT7）是糖胺聚糖（GAG）链生物合成中的关键酶。天然和合成木糖苷可通过充当β4GalT7的抑制剂或底物来抑制和引发GAG合成。在本报告中，我们利用羟基氧烷作为脱氧的木糖苷类似物来阐明半乳糖基化和/或抑制所需的最小蛋白质-配体相互作用。对映体纯物质是使用手性池方法合成的，而相应的外消旋物则是从简单的起始原料中获得的。β4GalT7测定的结果表明，在恶烷环上的单个羟基不足以诱导半乳糖基化或抑制，这意味着需要存在至少两个取代基，其中一个是3-OH。

  DOI：

  10.1016/j.tetlet.2017.07.078
• 作为产物：
  描述：

  2-naphthyl 2,4-di-O-benzyl-β-D-xylopyranoside 在 咪唑 、 盐酸 、 偶氮二异丁腈 、 palladium 10% on activated carbon 、 氢气 、 三正丁基氢锡 、 sodium hydride 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 7.5h， 生成 2-naphthyl 3-deoxy-β-D-erythropyranoside
  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.
• Hydroxylated oxanes as xyloside analogs for determination of the minimal binding requirements of β4GalT7
  作者：Karin Thorsheim、Sebastian Clementson、Emil Tykesson、Dennis Bengtsson、Daniel Strand、Ulf Ellervik

  DOI：10.1016/j.tetlet.2017.07.078

  日期：2017.8

  both inhibit and prime GAG synthesis by acting as inhibitors or substrates for β4GalT7. In this report, we exploit hydroxylated oxanes as deoxygenated xyloside analogs to clarify the minimum protein-ligand interactions required for galactosylation and/or inhibition. Enantiomerically pure substances were synthesized using a chiral pool approach whereas the corresponding racemates were obtained from simple

  β-1,4-半乳糖基转移酶7（β4GalT7）是糖胺聚糖（GAG）链生物合成中的关键酶。天然和合成木糖苷可通过充当β4GalT7的抑制剂或底物来抑制和引发GAG合成。在本报告中，我们利用羟基氧烷作为脱氧的木糖苷类似物来阐明半乳糖基化和/或抑制所需的最小蛋白质-配体相互作用。对映体纯物质是使用手性池方法合成的，而相应的外消旋物则是从简单的起始原料中获得的。β4GalT7测定的结果表明，在恶烷环上的单个羟基不足以诱导半乳糖基化或抑制，这意味着需要存在至少两个取代基，其中一个是3-OH。