(2R,3S,4R,5R,6R)-5-acetamido-2-(acetoxymethyl)-6-((hydroxy((hydroxy((11-phenoxyundecyl)oxy)phosphoryl)oxy)phosphoryl)oxy)tetrahydro-2H-pyran-3,4-diyl diacetate | 849588-05-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3S,4R,5R,6R)-5-acetamido-2-(acetoxymethyl)-6-((hydroxy((hydroxy((11-phenoxyundecyl)oxy)phosphoryl)oxy)phosphoryl)oxy)tetrahydro-2H-pyran-3,4-diyl diacetate
• CAS: 849588-05-2
• 化学式: C₃₁H₄₉NO₁₆P₂
• 分子量: 753.675
• InChiKey: SGUIBJOVAJWQIK-JQWMYKLHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.48
• 重原子数：
  50.0
• 可旋转键数：
  23.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  228.75
• 氢给体数：
  3.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  (2R,3S,4R,5R,6R)-5-acetamido-2-(acetoxymethyl)-6-((hydroxy((hydroxy((11-phenoxyundecyl)oxy)phosphoryl)oxy)phosphoryl)oxy)tetrahydro-2H-pyran-3,4-diyl diacetate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 生成
  参考文献：
  名称：

  A very simple synthesis of GlcNAc-α-pyrophosphoryl-decanol: A substrate for the assay of a bacterial galactosyltransferase

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2007.11.031
• 作为产物：
  描述：

  2-[(11-bromoundecyl)oxy]tetrahydro-2H-pyran 在 palladium on activated charcoal 四氮唑 、 氢氧化钾 、 氢气 、 甲基三辛基氯化铵 、 对甲苯磺酸 、 间氯过氧苯甲酸 、 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 72.0h， 生成 (2R,3S,4R,5R,6R)-5-acetamido-2-(acetoxymethyl)-6-((hydroxy((hydroxy((11-phenoxyundecyl)oxy)phosphoryl)oxy)phosphoryl)oxy)tetrahydro-2H-pyran-3,4-diyl diacetate
  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