(benzyloxyhydroxyphosphoryl)acetic acid benzyl ester | 214918-99-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (benzyloxyhydroxyphosphoryl)acetic acid benzyl ester
• 英文别名: (2-Oxo-2-phenylmethoxyethyl)-phenylmethoxyphosphinic acid
• CAS: 214918-99-7
• 化学式: C₁₆H₁₇O₅P
• 分子量: 320.282
• InChiKey: QJKDHSYTZLNLTR-UHFFFAOYSA-N

物化性质

• 沸点：
  482.8±55.0 °C(Predicted)
• 密度：
  1.294±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-十一烷醇,11-苯氧基- 、 (benzyloxyhydroxyphosphoryl)acetic acid benzyl ester 在 三苯基膦 、 偶氮二甲酸二异丙酯 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 以83%的产率得到[benzyloxy(11-phenoxyundecyloxy)phosphinyl]acetic acid benzyl ester
  参考文献：
  名称：

  Synthesis of acceptor substrate analogs for the study of glycosyltransferases involved in the second step of the biosynthesis of O-antigen repeating units

  摘要：

  O-antigens of Gram negative bacteria are polysaccharides covalently attached to lipopolysaccharides (LPS) that have roles as virulence factors. Due to the lack of defined substrates for in vitro assays only a few of the enzymes involved in the biosynthesis of O-antigens have been studied. Many O-antigens have GlcNAc at the reducing end of the oligosaccharide chain linked to pyrophosphate-lipid. We therefore designed and synthesized a series of GlcNAc-pyrophosphate-lipid analogs of the natural GlcNAc-pyrophosphate-undecaprenol acceptor substrate for studies of the acceptor specificities of O-antigen biosynthetic enzymes. We synthesized analogs with modifications of the pyrophosphate bond as well as the lipid chain. These compounds will be useful for the specificity studies of many bacterial glycosyltransferases. Knowledge of the substrate specificities is the basis for the development of specific glycosyltransferase inhibitors that could block O-antigen biosynthesis. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2009.12.022
• 作为产物：
  描述：

  dibenzylphosphonoacetic acid 在 三乙烯二胺 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 10.0h， 生成 (benzyloxyhydroxyphosphoryl)acetic acid benzyl ester
  参考文献：
  名称：

  酶促稳定的GDP类似物的合成，用于与转导蛋白（视觉感光体的G蛋白）进行结合研究。

  摘要：

  进行了五种鸟嘌呤二磷酸鸟嘌呤（GDP）的酶促稳定类似物的合成。焦磷酸部分依次被丙二酸酯，乙酰膦酸酯，膦酰基乙酸酯，亚甲基双膦酸酯和亚氨基二磷酸酯基团模拟。所有化合物都是通过合成一个瞬态完全保护的核苷二磷酸类似物来制备的，最后的脱保护步骤是通过催化氢解来实现的。已针对视觉感光器的G蛋白转导素评估了化合物的生物学特性。然后制备并评估了三种在糖上和碱基上不同位置带有连接子的鸟嘌呤亚氨基二磷酸衍生物，从而对转导蛋白的GDP结合位点有所了解。

  DOI：

  10.1021/jo9806207

文献信息

• ANTI-BACTERIAL COMPOSITIONS AND METHODS INCLUDING TARGETING VIRULENCE FACTORS OF STAPHYLOCOCCUS AUREUS
  申请人：Oldfield Eric

  公开号：US20120022024A1

  公开（公告）日：2012-01-26

  This disclosure relates to compositions and methods including for the inhibition, prevention, and/or treatment of microbial infections, including infections from such pathogens as Staphylococcus aureus.

  本公开涉及包括用于抑制、预防和/或治疗微生物感染的组合物和方法，包括对金黄色葡萄球菌等病原体引起的感染。
• [EN] ANTI-BACTERIAL COMPOSITIONS AND METHODS INCLUDING TARGETING VIRULENCE FACTORS OF STAPHYLOCOCCUS AUREUS<br/>[FR] COMPOSITIONS ANTI-BACTÉRIENNES ET PROCÉDÉS COMPRENANT LE CIBLAGE DE FACTEURS DE VIRULENCE DE STAPHYLOCOCCUS AUREUS
  申请人：UNIV ILLINOIS

  公开号：WO2010123599A9

  公开（公告）日：2011-02-17

  [EN] This disclosure relates to compositions and methods including for the inhibition, prevention, and/or treatment of microbial infections, including infections from such pathogens as Staphylococcus aureus.
  [FR] L'invention se rapporte à des compositions et à des procédés notamment pour l'inhibition, la prévention, et/ou le traitement d'infections microbiennes, y compris des infections par des agents pathogènes tels que Staphylococcus aureus.
• Synthesis of Enzymatically Stable Analogues of GDP for Binding Studies with Transducin, the G-Protein of the Visual Photoreceptor
  作者：Stéphane Vincent、Sonya Grenier、Alain Valleix、Christian Salesse、Luc Lebeau、Charles Mioskowski

  DOI：10.1021/jo9806207

  日期：1998.10.1

  final deprotection step was achieved by catalytic hydrogenolysis. The biological properties of the compounds have been evaluated toward transducin, the G-protein of the visual photoreceptor. Three guanosine imidodiphosphate derivatives bearing a linker at different positions on the sugar and on the base were then prepared and evaluated, giving some insight into the GDP binding site of transducin.

  进行了五种鸟嘌呤二磷酸鸟嘌呤（GDP）的酶促稳定类似物的合成。焦磷酸部分依次被丙二酸酯，乙酰膦酸酯，膦酰基乙酸酯，亚甲基双膦酸酯和亚氨基二磷酸酯基团模拟。所有化合物都是通过合成一个瞬态完全保护的核苷二磷酸类似物来制备的，最后的脱保护步骤是通过催化氢解来实现的。已针对视觉感光器的G蛋白转导素评估了化合物的生物学特性。然后制备并评估了三种在糖上和碱基上不同位置带有连接子的鸟嘌呤亚氨基二磷酸衍生物，从而对转导蛋白的GDP结合位点有所了解。
• Synthesis of acceptor substrate analogs for the study of glycosyltransferases involved in the second step of the biosynthesis of O-antigen repeating units
  作者：John G. Riley、Changchang Xu、Inka Brockhausen

  DOI：10.1016/j.carres.2009.12.022

  日期：2010.3

  O-antigens of Gram negative bacteria are polysaccharides covalently attached to lipopolysaccharides (LPS) that have roles as virulence factors. Due to the lack of defined substrates for in vitro assays only a few of the enzymes involved in the biosynthesis of O-antigens have been studied. Many O-antigens have GlcNAc at the reducing end of the oligosaccharide chain linked to pyrophosphate-lipid. We therefore designed and synthesized a series of GlcNAc-pyrophosphate-lipid analogs of the natural GlcNAc-pyrophosphate-undecaprenol acceptor substrate for studies of the acceptor specificities of O-antigen biosynthetic enzymes. We synthesized analogs with modifications of the pyrophosphate bond as well as the lipid chain. These compounds will be useful for the specificity studies of many bacterial glycosyltransferases. Knowledge of the substrate specificities is the basis for the development of specific glycosyltransferase inhibitors that could block O-antigen biosynthesis. (C) 2010 Elsevier Ltd. All rights reserved.