UDP-N-acetylmuramic acid α-anomer | 18867-75-9

• 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 α-anomer
• 英文别名: uridine-5'-diphosphate-N-acetylmuramine；UDP-N-acetylmuramic acid；UDP-MurNAc；O^5'-{2-[2-acetylamino-O³-((R)-1-carboxy-ethyl)-2-deoxy-α-D-glucopyranosyloxy]-1,2-dihydroxy-diphosphoryl}-uridine；O^5'-{2-[2-Acetylamino-O³-((R)-1-carboxy-aethyl)-2-desoxy-α-D-glucopyranosyloxy]-1,2-dihydroxy-diphosphoryl}-uridin；(2r)-2-{[(2r,3r,4r,5s,6r)-3-(Acetylamino)-2-{[(S)-{[(R)-{[(2r,3s,4r,5r)-5-(2,4-Dioxo-3,4-Dihydropyrimidin-1(2h)-Yl)-3,4-Dihydroxytetrahydrofuran-2-Yl]methoxy}(Hydroxy)phosphoryl]oxy}(Hydroxy)phosphoryl]oxy}-5-Hydroxy-6-(Hydroxymethyl)tetrahydro-2h-Pyran-4-Yl]oxy}propanoic Acid；(2R)-2-[(2R,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: 18867-75-9
• 化学式: C₂₀H₃₁N₃O₁₉P₂
• 分子量: 679.422
• InChiKey: NQBRVZNDBBMBLJ-MQTLHLSBSA-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：

  UDP-N-acetylmuramic acid α-anomer 在 sodium hydroxide 、 水 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 UDP-MurNAc-L-Ala-D-Glu-γ-L-Lys-D-Ala-D-Ala
  参考文献：
  名称：

  一种有效的化学酶策略，用于合成野生型和耐万古霉素的细菌细胞壁前体：UDP-N-乙酰基muramyl-肽。

  摘要：

  DOI：

  10.1021/ja011708w
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 铂 作用下， 生成 UDP-N-acetylmuramic acid α-anomer
  参考文献：
  名称：

  Gunetileke; Anwar, Journal of Biological Chemistry, 1968, vol. 243, p. 5770,5776

  摘要：

  DOI：

文献信息

• Optimization of UDP-N-acetylmuramic acid synthesis
  作者：Humljan, Jan、Starcevic、Car、Stefanic Anderluh、Kocjan、Jenko、Urleb

  DOI：10.1691/ph.2008.7675

  日期：——

  UDP-N-acetylmuramic acid (UDP-MurNAc) is a substrate of MurC, an important enzyme in the intracellular pathway of bacterial peptidoglycan biosynthesis. Various approaches towards preparation of UDP-MurNAc have been published but these synthetic preparations were shown to include many problematic steps. An optimization study with the focus on muramyl phosphate and UMP-morpholidate coupling was performed, resulting in a synthetic procedure enabling robust and easily reproducible production on a multi-gram scale.

  UDP-N-乙酰肟酸（UDP-MurNAc）是MurC的底物，MurC是细菌肽聚糖生物合成细胞内途径中的重要酶。已经发布了多种制备UDP-MurNAc的方法，但这些合成准备显示出许多问题步骤。进行了一项优化研究，重点关注肽聚糖磷酸盐和UMP-吗啉酸酯的耦合，最终实现了一种合成程序，使得在多克朗规模上进行稳健且易于复制的生产成为可能。
• 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。
• Metabolic pathway assay
  申请人：Merck & Co., Inc.

  公开号：US05891621A1

  公开（公告）日：1999-04-06

  An in vitro screening assay which identifies enzyme inhibitors and allows for the simultaneous assay of many enzymes. Enzyme, substrate, co-factor, etc. concentrations are optimized so that inhibitors of any one of the enzymes in the pathway are equally likely to be detected. Necessarily, the flux of substrate through each enzyme should be nearly the same during the assay, i.e., each of the enzyme catalyzed steps must be equally rate-limiting. Preferably, optimal assay conditions are predicted by computer modeling. Further, the pathway conditions are optimized through variation of enzyme, starting substrate, co-substrate and co-factor concentrations. A positive response is initially detected as a change in the amount of the product generated at the end of the enzyme cascade as compared to a standard. A sample producing a positive result can be deconvoluted.

  一种体外筛选酶抑制剂的方法，允许同时检测多种酶。酶、底物、辅因子等浓度被优化，以便能够同等可能地检测到通路中任何一个酶的抑制剂。必须保证在检测过程中，每个酶催化步骤的底物通量几乎相同，即每个酶催化步骤必须同等限制速率。最好通过计算机建模预测最佳检测条件。此外，通过变化酶、起始底物、共同底物和辅助因子的浓度来优化通路条件。正反应最初被检测为与标准相比，酶级联结束时产生的产物数量的变化。产生阳性结果的样品可以被解析。
• Cofactor‐Driven Cascade Reactions Enable the Efficient Preparation of Sugar Nucleotides
  作者：Yuan Zheng、Jiabin Zhang、Jeffrey Meisner、Wanjin Li、Yawen Luo、Fangyu Wei、Liuqing Wen

  DOI：10.1002/anie.202115696

  日期：2022.5.9

  The complex de novo biosynthesis of sugar nucleotides was reorganized as cascade reactions. The cascade reactions were driven toward the formation of the target sugar nucleotides through the addition of an excess amount of a cofactor provided by a cofactor regeneration system, thus resulting in high synthetic yields.

  糖核苷酸的复杂从头生物合成被重组为级联反应。通过添加辅因子再生系统提供的过量辅因子，将级联反应驱动到目标糖核苷酸的形成，从而产生高合成产量。
• Multi gram synthesis of UDP- N -acetylmuramic acid
  作者：C. Dini、N. Drochon、P. Ferrari、J. Aszodi

  DOI：10.1016/s0960-894x(99)00638-1

  日期：2000.1

  As part of an effort to discover novel antibacterial agents, a new and efficient synthesis was established in order to provide a large amount of UDP-N-acetylmuramic acid (UDP-MurNAc). (C) 2000 Elsevier Science Ltd. All rights reserved.