ficaprenol-11 | 11023-57-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: ficaprenol-11
• 英文别名: (2Z,6Z,10Z,14Z,18Z,22Z,26Z,30E,34E,38E)-3,7,11,15,19,23,27,31,35,39,43-undecamethyltetratetraconta-2,6,10,14,18,22,26,30,34,38,42-undecaen-1-ol；prenol-11 α-cis；ficaprenol 11；undecaprenol；(2Z,6Z,10Z,14Z,18Z,22Z,26Z,30E,34E,38E)-3,7,11,15,19,23,27,31,35,39,43-undecamethyl-tetratetraconta-2,6,10,14,18,22,26,30,34,38,42-undecaen-1-ol；(Z,Z,Z,Z,Z,Z,Z,E,E,E)-undecaprenol
• CAS: 11023-57-7；15575-14-1；20438-12-4；28979-23-9；50426-50-1；59685-00-6；73367-16-5；88200-23-1；26296-50-4
• 化学式: C₅₅H₉₀O
• 分子量: 767.319
• InChiKey: TXKJNHBRVLCYFX-RTRZQXHFSA-N

物化性质

• 沸点：
  777.0±29.0 °C(Predicted)
• 密度：
  0.890±0.06 g/cm3(Predicted)
• 溶解度：
  溶于氯仿、二氯甲烷、乙酸乙酯、DMSO、丙酮等。

计算性质

• 辛醇/水分配系数(LogP)：
  19.6
• 重原子数：
  56
• 可旋转键数：
  31
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  ficaprenol-11 在 吡啶 、 六甲基磷酰三胺 、 二苯并-18-冠醚-6 、 正丁基锂 、 氨 、 sodium 、 三溴化磷 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 0.33h， 生成 3,7,11,15,19,23,27,31,35,39,43,47-dodecamethyloctatetraconta-2E,6Z,10Z,14Z,18Z,22Z,26Z,30Z,34E,38E,42E,46-dodecaen-1-ol
  参考文献：
  名称：

  Stage synthesis of three modified phenols

  摘要：

  DOI：

  10.1007/bf00959372
• 作为产物：
  描述：

  1-((2Z,6Z,10Z,14Z,18Z,22Z,26Z,30E,34E,38E)-1-benzyloxy-17-tosyl-3,7,11,15,19,23,27,31,35,39,43-undecamethyltetratetraconta-2,6,10,14,18,22,26,30,34,38,42-undecaen-9-yl)sulfonyl-4-methylbenzene 在 lithium 、 乙胺 、 天然橡胶 作用下， 以 乙醚 、 甲醇 为溶剂， 反应 1.0h， 以65%的产率得到ficaprenol-11
  参考文献：
  名称：

  Synthesis of undecaprenyl pyrophosphate-linked glycans as donor substrates for bacterial protein N-glycosylation

  摘要：

  Synthesis of undecaprenyl pyrophosphate (Und-PP)-linked glycans is described. Bacterial ([E](3),[Z](7))-undecaprenol was synthesized from trans-geranylgeranyl sulfone and isoprenoid building blocks, which was converted to undecaprenyl phosphate (Und-P). It was coupled with glycosyl phosphates to afford Und-PP-linked glycans, including core trisaccharide of Campylobacter jejuni N-glycan. Our synthetic method for Und-PP-linked glycan would provide various substrates as a useful tool for systematic analysis of bacterial protein N-glycosylation. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.06.032

文献信息

• Enzymatic Synthesis of Lipid II and Analogues
  作者：Lin-Ya Huang、Shih-Hsien Huang、Ya-Chih Chang、Wei-Chieh Cheng、Ting-Jen R. Cheng、Chi-Huey Wong

  DOI：10.1002/anie.201402313

  日期：2014.7.28

  polymerizes lipid II into peptidoglycan and is one of the most favorable targets because of its vital role in peptidoglycan synthesis. Described in this study is a practical enzymatic method for the synthesis of lipid II, coupled with cofactor regeneration, to give the product in a 50–70 % yield. This development depends on two key steps: the overexpression of MraY for the synthesis of lipid I and the

  抗生素抗性的出现促使人们积极研究具有新作用方式的抗生素。在所有必需的细菌蛋白中，转糖基化酶将脂质II聚合成肽聚糖，并且由于其在肽聚糖合成中的重要作用而成为最有利的靶标之一。在这项研究中描述的是一种实用的酶促方法，可以合成脂质II，并辅以辅因子再生，从而以50-70％的收率获得该产品。这一发展取决于两个关键步骤：MraY在脂质I合成中的过表达和十一碳烯醇激酶在制备聚戊二烯磷酸酯中的应用。该方法进一步应用于脂质II类似物的合成。已经发现，MraY和十一碳烯醇激酶可以接受包含各种长度和构型的多种脂质。还评估了脂质II类似物对细菌转葡聚糖酶的活性。
• Synthesis of a Comprehensive Polyprenol Library for the Evaluation of Bacterial Enzyme Lipid Substrate Specificity
  作者：Baolin Wu、Robert Woodward、Liuqing Wen、Xuan Wang、Guohui Zhao、Peng George Wang

  DOI：10.1002/ejoc.201301089

  日期：2013.12

  Polyprenols, a type of universal glycan lipid carrier, play important roles for glycan bio-assembly in wide variety of living systems. Chemical synthesis of natural polyisoprenols such as undecaprenol and dolichols, but especially their homologs, could serves as a powerful molecular tool to dissect and define the functions of enzymes involved in glycan biosynthesis. In this paper, we report an efficient

  多元醇是一种通用的聚糖脂质载体，在多种生物系统中对聚糖的生物组装起着重要的作用。天然的聚异戊二烯，例如十一碳烯醇和二元醇的化学合成，尤其是它们的同系物，可以作为一种强大的分子工具来分析和确定参与聚糖生物合成的酶的功能。在本文中，我们报告了一种有效且可靠的方法，该方法通过使用关键的双功能（Z，Z）-二异戊二烯结构单元的碱基介导的迭代偶联方法来构建此类疏水分子。还证明了与N-乙酰基-D-葡糖胺（GalNAc）与一组合成的脂质类似物形成聚戊二烯焦磷酸连接的GalNAc（GalNAc-PP-脂质）缀合物的连接。
• Better Substrates for Bacterial Transglycosylases
  作者：Xiang-Yang Ye、Mei-Chu Lo、Livia Brunner、Deborah Walker、Daniel Kahne、Suzanne Walker

  DOI：10.1021/ja010028q

  日期：2001.4.1
• Chemoenzymatic synthesis of polyprenyl phosphates
  作者：Meredith D. Hartley、Angelyn Larkin、Barbara Imperiali

  DOI：10.1016/j.bmc.2008.03.025

  日期：2008.5

  Polyprenyl phosphates, including undecaprenyl phosphate and dolichyl phosphate, are essential intermediates in several important biochemical pathways including N-linked protein glycosylation in eukaryotes and prokaryotes and prokaryotic cell wall biosynthesis. Herein, we describe the evaluation of three potential undecaprenol kinases as agents for the chemoenzymatic synthesis of polyprenyl phosphates. Target enzymes were expressed in crude cell envelope fractions and quantified via the use of luminescent lanthanide-binding tags (LBTs). The Streptococcus mutans diacylglycerol kinase (DGK) was shown to be a very useful agent for polyprenol phosphorylation using ATP as the phosphoryl transfer agent. In addition, the S. mutans DGK can be coupled with two Campylobacter jejuni glycosyltransferases involved in N-linked glycosylation to efficiently biosynthesize the undecaprenyl pyrophosphate-linked disaccharide needed for studies of PglB, the C. jejuni oligosaccharyl transferase. (C) 2008 Elsevier Ltd. All rights reserved.
• Phosphorylation of Polyprenols via Their Trichloroacetimidates
  作者：Leonid L. Danilov、Vladimir N. Shibaev、Nikolai K. Kochetkov

  DOI：10.1055/s-1984-30853

  日期：——