UDP-N-acetylmuramic acid β-anomer | 2316-24-7

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷酸
• 英文名称: UDP-N-acetylmuramic acid β-anomer
• 英文别名: UDP-N-acetylmuramic acid；(2R)-2-[(2S,3R,4R,5S,6R)-3-acetamido-2-[[[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxypropanoic acid
• CAS: 2316-24-7
• 化学式: C₂₀H₃₁N₃O₁₉P₂
• 分子量: 679.422
• InChiKey: NQBRVZNDBBMBLJ-DAUPKUNTSA-N

物化性质

• 密度：
  1.80±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -6.1
• 重原子数：
  44
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  327
• 氢给体数：
  9
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  L-丙氨酸 、 UDP-N-acetylmuramic acid β-anomer 在 DL-dithiothreitol 、 三羟甲基甲胺基丙磺酸 、 5’-三磷酸腺苷 、 magnesium chloride 作用下， 以 水 为溶剂， 反应 5.0h， 以79%的产率得到UDP-N-Acetylmuramyl-L-alanine
  参考文献：
  名称：

  Preparative Enzymatic Synthesis and Characterization of the Cytoplasmic Intermediates of Murein Biosynthesis

  摘要：

  The first six cytoplasmic intermediates of murein biosynthesis (2-7) have been prepared in high yield (>60%) and at preparative scale (10-100 mg) using purified enzymes of the murein biosynthetic pathway (MurA-MurF). For at least three of these compounds, 5, 6, and 7, this is the first high-yield synthesis and purification by any means that has been reported. Detailed spectroscopic and analytical data accompany each of the six compounds and serve as reference standards for future work. The availability of these intermediates will facilitate the study of the murein pathway enzymes MurA-MurF, all of which are validated antibacterial targets.

  DOI：

  10.1021/ja983850b
• 作为产物：
  描述：

  uridine-5’-diphospho-N-acetyl-glucosamine 、 phosphoenol pyruvate hexaammonium salt 在 DL-dithiothreitol 、 三羟甲基甲胺基丙磺酸 、 还原型辅酶II(NADPH)四钠盐 作用下， 以 水 为溶剂， 反应 5.0h， 以87%的产率得到UDP-N-acetylmuramic acid β-anomer
  参考文献：
  名称：

  Preparative Enzymatic Synthesis and Characterization of the Cytoplasmic Intermediates of Murein Biosynthesis

  摘要：

  The first six cytoplasmic intermediates of murein biosynthesis (2-7) have been prepared in high yield (>60%) and at preparative scale (10-100 mg) using purified enzymes of the murein biosynthetic pathway (MurA-MurF). For at least three of these compounds, 5, 6, and 7, this is the first high-yield synthesis and purification by any means that has been reported. Detailed spectroscopic and analytical data accompany each of the six compounds and serve as reference standards for future work. The availability of these intermediates will facilitate the study of the murein pathway enzymes MurA-MurF, all of which are validated antibacterial targets.

  DOI：

  10.1021/ja983850b

文献信息

• Synthesis of α and β anomers of UDP-N-acetylmuramic acid
  作者：Didier Blanot、Geneviève Auger、Dominique Liger、Jean van Heijenoort

  DOI：10.1016/0008-6215(94)90009-4

  日期：1994.1

  (UDP-MurNAc) derivatives are substrates for several cytoplasmics steps of the synthesis of bacterial peptidoglycan (Park, 1952). Their availability is a prerequisite for developing the detailed study of the synthetases catalyzing these reactions. Since they are not commercial compounds, they have to be prepared from bacterial cells in which they accumulate under specific conditions. However, such procedures

  UDP-N-乙酰基muramyl（UDP-MurNAc）衍生物是细菌肽聚糖合成中几个胞质步骤的底物（Park，1952年）。它们的可用性是开展详细研究催化这些反应的合成酶的先决条件。由于它们不是市售化合物，因此必须从在特定条件下会在其中积累的细菌细胞中制备它们。但是，这样的过程冗长而乏味，并且收率通常很低。另一种方法是大规模化学合成UDP-N-乙酰基尿酸，并将其用作其他UDP-MurNAc前体的体外酶促制备的起始材料。在此通讯中，我们希望报告UDP-MurNAc的全部综合信息。
• Preparative Enzymatic Synthesis and Characterization of the Cytoplasmic Intermediates of Murein Biosynthesis
  作者：Sreelatha G. Reddy、Sherman T. Waddell、David W. Kuo、Kenny K. Wong、David L. Pompliano

  DOI：10.1021/ja983850b

  日期：1999.2.1

  The first six cytoplasmic intermediates of murein biosynthesis (2-7) have been prepared in high yield (>60%) and at preparative scale (10-100 mg) using purified enzymes of the murein biosynthetic pathway (MurA-MurF). For at least three of these compounds, 5, 6, and 7, this is the first high-yield synthesis and purification by any means that has been reported. Detailed spectroscopic and analytical data accompany each of the six compounds and serve as reference standards for future work. The availability of these intermediates will facilitate the study of the murein pathway enzymes MurA-MurF, all of which are validated antibacterial targets.