(6-hydroxy-2-naphthyl)-2,3,4-tri-O-acetyl-β-D-xylopyranoside | 940284-52-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (6-hydroxy-2-naphthyl)-2,3,4-tri-O-acetyl-β-D-xylopyranoside
• 英文别名: (6-hydroxynaphthalen-2-yl)2,3,4-Tri-O-acetyl-β-D-xylopyranoside
• CAS: 940284-52-6
• 化学式: C₂₁H₂₂O₉
• 分子量: 418.4
• InChiKey: BYJHWDHFDPVMAX-MHTWAQMVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.08
• 重原子数：
  30.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  117.59
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (6-hydroxy-2-naphthyl)-2,3,4-tri-O-acetyl-β-D-xylopyranoside 在 sodium methylate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 2-(6-(5-dimethylamino-naphthalene-1-sulfonyloxy)-naphthyl)-β-D-xylopyranoside
  参考文献：
  名称：

  Evaluation of fluorescently labeled xylopyranosides as probes for proteoglycan biosynthesis

  摘要：

  A new fluorescent analog to the antiproliferative 2-(6-hydroxynaphthyl)-beta-D-xylopyranoside has been synthesized and tested on a T24 cell line. The new analog was efficiently uptaken by the T24 cells but did not initiate priming of GAG chains. The results are similar to other fluorescently labeled analogs and we propose that these compounds are too large and unpolar to efficiently function as GAG-primers. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.01.063
• 作为产物：
  描述：

  2-acetoxy-6-hydroxynaphthalene 在 potassium cyanide 、 三氟化硼乙醚 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.92h， 生成 (6-hydroxy-2-naphthyl)-2,3,4-tri-O-acetyl-β-D-xylopyranoside
  参考文献：
  名称：

  Evaluation of fluorescently labeled xylopyranosides as probes for proteoglycan biosynthesis

  摘要：

  A new fluorescent analog to the antiproliferative 2-(6-hydroxynaphthyl)-beta-D-xylopyranoside has been synthesized and tested on a T24 cell line. The new analog was efficiently uptaken by the T24 cells but did not initiate priming of GAG chains. The results are similar to other fluorescently labeled analogs and we propose that these compounds are too large and unpolar to efficiently function as GAG-primers. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.01.063

文献信息

• Azide-Functionalized Naphthoxyloside as a Tool for Glycosaminoglycan Investigations
  作者：Daniel Willén、Roberto Mastio、Zackarias Söderlund、Sophie Manner、Gunilla Westergren-Thorsson、Emil Tykesson、Ulf Ellervik

  DOI：10.1021/acs.bioconjchem.1c00473

  日期：2021.12.15

  We present a xylosylated naphthoxyloside carrying a terminal azide functionality that can be used for conjugation using click chemistry. We show that this naphthoxyloside serves as a substrate for β4GalT7 and induces the formation of soluble glycosaminoglycan (GAG) chains with physiologically relevant lengths and sulfation patterns. Finally, we demonstrate its usefulness by conjugation to the Alexa Fluor 647 and TAMRA fluorophores and coupling to a surface plasmon resonance chip for interaction studies with the hepatocyte growth factor known to interact with the GAG heparan sulfate.

  我们展示了一种带有末端叠氮功能的木糖化萘基木糖苷，该物质可用于点击化学偶联反应。我们证明，这种萘基木糖苷可以作为β4GalT7的底物，并诱导形成具有生理相关长度和硫酸化模式的溶性糖胺聚糖（GAG）链。最后，我们通过将其与Alexa Fluor 647和TAMRA荧光团偶联，并结合到表面等离子共振芯片上，展示了其在研究与肝细胞生长因子（已知与糖胺聚糖类肝素硫酸结合）相互作用方面的实用性。
• Disubstituted naphthyl β-D-xylopyranosides: Synthesis, GAG priming, and histone acetyltransferase (HAT) inhibition
  作者：Karin Thorsheim、Andrea Persson、Anna Siegbahn、Emil Tykesson、Gunilla Westergren-Thorsson、Katrin Mani、Ulf Ellervik

  DOI：10.1007/s10719-016-9662-6

  日期：2016.4

  Xylosides are a group of compounds that can induce glycosaminoglycan (GAG) chain synthesis independently of a proteoglycan core protein. We have previously shown that the xyloside 2-(6-hydroxynaphthyl)β-D-xylopyranoside has a tumor-selective growth inhibitory effect both in vitro and in vivo, and that the effect in vitro was correlated to a reduction in histone H3 acetylation. In addition, GAG chains have previously been reported to inhibit histone acetyltransferases (HAT). To investigate if xylosides, or the corresponding xyloside-primed GAG chains, can be used as HAT inhibitors, we have synthesized a series of naphthoxylosides carrying structural motifs similar to the aromatic moieties of the known HAT inhibitors garcinol and curcumin, and studied their biological activities. Here, we show that the disubstituted naphthoxylosides induced GAG chain synthesis, and that the ones with at least one free phenolic group exhibited moderate HAT inhibition in vitro, without affecting histone H3 acetylation in cell culture. The xyloside-primed GAG chains, on the other hand, had no effect on HAT activity, possibly explaining why the effect of the xylosides on histone H3 acetylation was absent in cell culture as the xylosides were recruited for GAG chain synthesis. Further investigations are required to find xylosides that are effective HAT inhibitors or xylosides producing GAG chains with HAT inhibitory effects.

  木糖苷是一类化合物，能独立于蛋白聚糖核心蛋白诱导糖胺聚糖（GAG）链的合成。我们之前已经证明，2-（6-羟基萘基）-β-D-吡喃木糖苷具有肿瘤特异性的生长抑制作用，无论是在体外还是在体内，而且体外效应与组蛋白H3乙酰化的减少有关。此外，已有报道称GAG链能够抑制组蛋白乙酰转移酶（HAT）。为了研究木糖苷或相应的以木糖苷为引物的GAG链是否能作为HAT抑制剂，我们合成了一系列含有与已知的HAT抑制剂——广藿香醇和姜黄素——的芳香基团相似的结构特征的萘基木糖苷，并研究了它们的生物活性。在这里，我们展示了二取代的萘基木糖苷能够诱导GAG链的合成，那些至少含有一个自由酚羟基的萘基木糖苷在体外表现出适度的HAT抑制作用，且不影响细胞培养中组蛋白H3的乙酰化。另一方面，以木糖苷为引物的GAG链对HAT活性没有影响，这可能解释了为什么木糖苷对组蛋白H3的乙酰化在细胞培养中没有影响，因为木糖苷被招募用于GAG链的合成。进一步的研究需要找到有效的HAT抑制性木糖苷或产生具有HAT抑制效应的GAG链的木糖苷。