(2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9-hexadecafluoro-10-(pyren-1-ylmethoxy)decyloxy)acetic acid | 917232-16-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: (2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9-hexadecafluoro-10-(pyren-1-ylmethoxy)decyloxy)acetic acid
• 英文别名: 2-(2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9-hexadecafluoro-10-(pyren-1-ylmethoxy)decyloxy)acetic acid；2-[2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9-Hexadecafluoro-10-(pyren-1-ylmethoxy)decoxy]acetic acid；2-[2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9-hexadecafluoro-10-(pyren-1-ylmethoxy)decoxy]acetic acid
• CAS: 917232-16-7
• 化学式: C₂₉H₁₈F₁₆O₄
• 分子量: 734.434
• InChiKey: XOWDUARNVWDLIJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.5
• 重原子数：
  49
• 可旋转键数：
  15
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  20

反应信息

• 作为反应物：
  描述：

  (2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9-hexadecafluoro-10-(pyren-1-ylmethoxy)decyloxy)acetic acid 在 四(三苯基膦)钯 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 78.0h， 生成
  参考文献：
  名称：

  The Effect of Receptor Clustering on Vesicle−Vesicle Adhesion

  摘要：

  As part of our studies into how the localization of cell adhesion molecules into lipid rafts may affect cell adhesion, we developed Cu(1), a synthetic copper(iminodiacetate)-capped receptor able to phase separate from fluid phospholipid bilayers. The extent to which Cu(1) clustered into adhesive patches on the surface of vesicles could be controlled by changing vesicle composition. Extensive receptor phase separation significantly enhanced vesicle-vesicle adhesion; only vesicles with adhesive patches (blue fluorescence) adhered to their conjugate histidine-coated vesicles (red fluorescence) to form large vesicle aggregates (shown).

  DOI：

  10.1021/ja0657612
• 作为产物：
  描述：

  2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9-hexadecafluoro-10-(pyren-1-ylmethoxy)decan-1-ol 、 溴乙酸 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 72.0h， 以76%的产率得到(2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9-hexadecafluoro-10-(pyren-1-ylmethoxy)decyloxy)acetic acid
  参考文献：
  名称：

  The Effect of Receptor Clustering on Vesicle−Vesicle Adhesion

  摘要：

  As part of our studies into how the localization of cell adhesion molecules into lipid rafts may affect cell adhesion, we developed Cu(1), a synthetic copper(iminodiacetate)-capped receptor able to phase separate from fluid phospholipid bilayers. The extent to which Cu(1) clustered into adhesive patches on the surface of vesicles could be controlled by changing vesicle composition. Extensive receptor phase separation significantly enhanced vesicle-vesicle adhesion; only vesicles with adhesive patches (blue fluorescence) adhered to their conjugate histidine-coated vesicles (red fluorescence) to form large vesicle aggregates (shown).

  DOI：

  10.1021/ja0657612

文献信息

• Assessing the cluster glycoside effect during the binding of concanavalin A to mannosylated artificial lipid rafts
  作者：Gavin T. Noble、Sabine L. Flitsch、Kwan Ping Liem、Simon J. Webb

  DOI：10.1039/b910976e

  日期：——

  weak intramembrane chelation of Con A. Despite this observation, concentrating the mannosyl lipids into artificial lipid rafts did not significantly improve affinity for Con A. This lack of a cluster glycoside effect was ascribed to lipid congestion inhibiting intra-raft chelation of Con A, and implies that glycolipids located in lipid rafts may not necessarily be preorganised for multivalent binding.

  具有全氟烷基膜锚的甘露糖基糖脂已经合成。当插入囊泡中时，这些甘露糖基脂质要么均匀地分散在表面上，要么存在胆固醇相分离成人造脂质筏。在1％mol / mol时，分散的甘露糖基脂质对Con A的亲和力比溶液中弱3倍，这可能反映了表面的空间封闭。但是，将膜负荷增加5倍，会使Con A的亲和力增加多达75％，并表明Con A的膜内螯合作用较弱。尽管有此观察结果，将甘露糖基脂质浓缩到人造脂质筏中并不能显着改善对Con A的亲和力。簇糖苷效应归因于脂质充血抑制了Con A的筏内螯合，并暗示位于脂质筏中的糖脂可能不一定是预先组织的以进行多价结合。
• Accelerated Enzymatic Galactosylation of <i>N</i>-Acetylglucosaminolipids in Lipid Microdomains
  作者：Gavin T. Noble、Faye L. Craven、Josef Voglmeir、Robert Šardzík、Sabine L. Flitsch、Simon J. Webb

  DOI：10.1021/ja302506t

  日期：2012.8.8

  A fluoro-tagged N-acetylglucosamine-capped glycolipid that can form lipid microdomains in fluid phospholipid bilayers has been shown to be enzymatically galactosylated by bovine beta(1,4)-galactosyltransferase. MALDI MS, HPLC, and LC-MS revealed that the rate of enzymatic transformation was significantly enhanced by lipid clustering; at a 1% mol/mol loading, clustered glycolipids were galactosylated 9-fold faster than glycolipids dispersed across the bilayer surface. The transformation of the GlcNAc "glycocalyx" into a Gal(beta 1-4)GlcNAc "glycocalyx" relabeled these vesicles, making them susceptible to agglutination by Erythrina cristagalli lectin (ECL). The kinetic parameters for this transformation revealed a lower apparent K-m when the substrate lipids were clustered, which is attributed to multivalent binding to an extended substrate cleft around the active site. These observations may have important implications where soluble enzymes act on substrates embedded within cellular lipid rafts.