11-phenoxyundecyl dihydrogen phosphate | 849480-71-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 11-phenoxyundecyl dihydrogen phosphate
• 英文别名: 11-Phenoxyundecyl dihydrogen phosphate
• CAS: 849480-71-3
• 化学式: C₁₇H₂₉O₅P
• 分子量: 344.388
• InChiKey: ZSADRMWXOZFBQH-UHFFFAOYSA-N

物化性质

• 沸点：
  489.7±37.0 °C(Predicted)
• 密度：
  1.132±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  23
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  11-phenoxyundecyl dihydrogen phosphate 在 magnesium chloride 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 生成
  参考文献：
  名称：

  B组链球菌血清型VIII荚膜多糖四糖重复单元的顺序一锅三酶合成

  摘要：

  β-1,4-鼠李糖基转移酶（Cps8R）、β-1,4-半乳糖基转移酶（Cps8J）和α-2,3-唾液酸转移酶（Cps8K）三种重组糖基转移酶的生化性质和功能鉴定系统地研究了B组链球菌(GBS)血清型VIII荚膜多糖(CPS)的四糖重复单元。随后，使用化学合成的 Glcα-PP-(CH 2 ) 11 -OPh 作为起始底物，将这些重组酶用于一锅三酶高效合成 GBS 血清型 VIII CPS 的四糖重复单元，其产率为87%。

  DOI：

  10.1002/cjoc.202100822
• 作为产物：
  描述：

  2-[(11-phenoxyundecyl)oxy]tetrahydro-2H-pyran 在 palladium on activated charcoal 四氮唑 、 氢气 、 对甲苯磺酸 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 16.5h， 生成 11-phenoxyundecyl dihydrogen phosphate
  参考文献：
  名称：

  Identification of a UDP-Gal: GlcNAc-R galactosyltransferase activity in Escherichia coli VW187

  摘要：

  A novel acceptor substrate for galactosyltransferase was synthesized containing GlcNAcalpha-pyrophosphate, covalently bound to a hydrophobic phenoxyundecyl moiety (GlcNAc alpha-PO3-PO3-(CH2)(11)-O-Phenyl). The new substrate was used to develop an assay for a galactosyltransferase activity from Escherichia coli strain VW187 that is involved in lipopolysaccharide synthesis and has not been studied by others. We showed that Gal was transferred from UDP-Gal to the novel acceptor substrate. This was a significant improvement over our previous preliminary assays of the enzyme using endogenous substrate, and showed that these synthetic substrates are useful for assaying enzymes that utilize lipid-bound substrates in O-chain synthesis in Gram-negative bacteria. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.11.077

文献信息

• Synthesis of P 1 -(11-phenoxyundecyl)-P 2 -(2-acetamido-2-deoxy-3- O -α- D -rhamnopyranosyl-α- D -glucopyranosyl) diphosphate and P 1 -(11-phenoxyundecyl)-P 2 -(2-acetamido-2-deoxy-3- O -β- D -galactopyranosyl-α- D -galactopyranosyl) diphosphate for the investigation of biosynthesis of O-antigenic polysaccharides in Pseudomonas aeruginosa and Escherichia coli O104
  作者：Vladimir Torgov、Leonid Danilov、Natalia Utkina、Vladimir Veselovsky、Inka Brockhausen

  DOI：10.1016/j.carres.2017.10.016

  日期：2017.12

  Two new phenoxyundecyl diphosphate sugars were synthesized for the first time: P1-(11-phenoxyundecyl)-P2- (2-acetamido-2-deoxy-3-O-α-D-rhamnopyranosyl-α-D-glucopyranosyl) diphosphate and P1-(11-phenoxyundecyl)-P2-(2-acetamido-2-deoxy-3-O-β-D-galactopyranosyl-α-D-galactopyranosyl) diphosphate to study the third step of biosynthesis of the repeating units of O-antigenic polysaccharides in Pseudomonas

  首次合成了两个新的苯氧基十一烷基二磷酸糖：P1-（11-苯氧基十一烷基）-P2-（2-乙酰氨基-2-脱氧-3-O-α-D-鼠李糖基吡喃糖基-α-D-葡萄糖基吡喃糖基）二磷酸和P1 -（11-苯氧基十一烷基）-P2-（2-乙酰氨基-2-脱氧-3-O-β-D-吡喃并吡喃糖基-α-D-吡喃并吡喃糖基）二磷酸酯，以研究O抗原重复单元的生物合成的第三步铜绿假单胞菌和大肠杆菌O104中的多糖分别。
• Biochemical studies of a β-1,4-rhamnoslytransferase from <i>Streptococcus pneumonia</i> serotype 23F
  作者：Hong Wang、Siqiang Li、Chenghe Xiong、Guoxia Jin、Zonggang Chen、Guofeng Gu、Zhongwu Guo

  DOI：10.1039/c8ob02795a

  日期：——

  A new β-rhamnoslytransferase Cps23FT from Streptococcus pneumonia serotype 23F was expressed and characterized. Its enzymatic activity and function were confirmed for the first time by utilizing enzymatically prepared dTDP-Rha and chemically synthesized Glcα-PP-(CH2)11-OPh as substrates. This reaction gave the desired disaccharide Rhaβ-1,4-Glcα-PP-(CH2)11-OPh in a good isolated yield (67%), suggesting

  表达和鉴定了一种新的来自肺炎链球菌血清型23F的β-鼠李糖基转移酶Cps23FT 。以酶法制备的dTDP-Rha和化学合成的Glcα-PP-（CH 2）11 -OPh为底物，首次证实了其酶活性和功能。该反应以良好的分离产率（67％）得到了所需的二糖Rhaβ-1,4-Glcα-PP-（CH 2）11 -OPh，表明Cps23FT作为合成复杂寡糖的工具酶的潜力。 β-鼠李糖基键。此外，Cps23FT的定点诱变显示其271 DKD 273 基序对于酶活性至关重要，最有可能是所需二价金属阳离子的结合位点。
• A very simple synthesis of GlcNAc-α-pyrophosphoryl-decanol: A substrate for the assay of a bacterial galactosyltransferase
  作者：Inka Brockhausen、E. Andreas Larsson、Ole Hindsgaul

  DOI：10.1016/j.bmcl.2007.11.031

  日期：2008.1

  Lipid-linked sugar pyrophosphates, such as GlcNAc-pyrophosphoryl undecaprenol, are important intermediates in the biosynthesis of cell-surface bacterial polysaccharides. It was recently demonstrated that much simpler lipids could substitute for undecaprenol while retaining biological activity, thus making efficient synthetic access to this class of compounds highly desirable. In order to facilitate the synthesis of pure substrates for bacterial glycosyltransferases, we have developed a simple 'two-pot' synthesis which we demonstrate here for GlcNAc-alpha-pyrophosphoryl-decanol (4). GlcNAc pyrophosphate, produced by mild periodate oxidation/beta-elimination of commercial UDP-GlcNAc, is alkylated using 1-iododecane to yield the target compound 4 in 39% yield. Compound 4 is shown to be an efficient acceptor for a bacterial galactosyltransferase. (c) 2007 Elsevier Ltd. All rights reserved.
• Simple synthesis of P 1-(11-phenoxyundecyl)-P 2-(2-acetamido-2-deoxy-α-D-galactopyranosyl) diphosphate
  作者：N. S. Utkina、L. L. Danilov、T. N. Druzhinina、V. V. Veselovskii

  DOI：10.1134/s1068162010060166

  日期：2010.11

  A simple method of the synthesis of P (1)-(11-phenoxyundecyl)-P (2)-(2-acetamido-2-deoxy-alpha-D-galactopyranosyl) diphosphate, which is a synthetic lipid acceptor for glycosyl transferases participating in the biosynthesis of O-antigenic polysaccharides of Gram-negative bacteria, is suggested.
• 11-Phenoxyundecyl phosphate as a 2-acetamido-2-deoxy-α-d-glucopyranosyl phosphate acceptor in O-antigen repeating unit assembly of Salmonella arizonae O:59
  作者：Tatyana N. Druzhinina、Leonid L. Danilov、Vladimir I. Torgov、Natalya S. Utkina、Nadezhda M. Balagurova、Vladimir V. Veselovsky、Alexander O. Chizhov

  DOI：10.1016/j.carres.2010.09.021

  日期：2010.12

  A synthesis of 11-phenoxyundecyl phosphate and its biochemical transformation (using GlcNAc-P transferase from Salmonella arizonae 0 59 membranes catalysing transfer of GlcNc-phosphate from UDP-GlcNAc on lipid-phosphate) into P(1)-11-phenoxyundecyl P(2)-2-acetamido-2-deoxy-alpha-D-glucopyranosyl diphosphate are described (C) 2010 Elsevier Ltd All rights reserved