(6-acetoxy-2-naphthyl)-2,3,4-tri-O-acetyl-β-D-xylopyranoside | 940284-51-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (6-acetoxy-2-naphthyl)-2,3,4-tri-O-acetyl-β-D-xylopyranoside
• 英文别名: 2-(6-O-acetylnaphthyl)-2,3,4-tri-O-acetyl-β-D-xylopyranoside；Xyl-2-Nap-6-OH, peracetylated；[(3R,4S,5R,6S)-4,5-diacetyloxy-6-(6-acetyloxynaphthalen-2-yl)oxyoxan-3-yl] acetate
• CAS: 940284-51-5
• 化学式: C₂₃H₂₄O₁₀
• 分子量: 460.438
• InChiKey: XKDPKSMGPYXANL-ACESQOTJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  124
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (6-acetoxy-2-naphthyl)-2,3,4-tri-O-acetyl-β-D-xylopyranoside 在 ammonium acetate 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 以84%的产率得到(6-hydroxy-2-naphthyl)-2,3,4-tri-O-acetyl-β-D-xylopyranoside
  参考文献：
  名称：

  Azide-Functionalized Naphthoxyloside as a Tool for Glycosaminoglycan Investigations

  摘要：

  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。

  DOI：

  10.1021/acs.bioconjchem.1c00473
• 作为产物：
  描述：

  2-acetoxy-6-hydroxynaphthalene 、 tetra-O-acetyl-β-D-xylopyranose 在 三氟化硼乙醚 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.25h， 以81%的产率得到(6-acetoxy-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

• Antiproliferative effects of peracetylated naphthoxylosides
  作者：Ulrika Nilsson、Mårten Jacobsson、Richard Johnsson、Katrin Mani、Ulf Ellervik

  DOI：10.1016/j.bmcl.2009.01.065

  日期：2009.3

  The antiproliferative activity, and the capability of priming of glycosaminoglycan chains, of two series of peracetylated mono- and bis-xylosylated dihydroxynaphthalenes have been investigated for normal HFL-1 cells, as well as transformed T24 cells, and compared to the unprotected analogs. Our data show increased antiproliferative activity upon peracetylation, but a loss of selectivity towards T24 cells. (C) 2009 Elsevier Ltd. All rights reserved.
• Evaluation of fluorescently labeled xylopyranosides as probes for proteoglycan biosynthesis
  作者：Richard Johnsson、Katrin Mani、Ulf Ellervik

  DOI：10.1016/j.bmcl.2007.01.063

  日期：2007.4

  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.
• 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。