2-acetamido-6-O-acetyl-3-O-[(R)-1-carboxyethyl]-2-deoxy-α-D-glucopyranoside-1-α-(diphenyl phophate) 1',4-lactone | 262853-72-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磷酸及其衍生物
• 英文名称: 2-acetamido-6-O-acetyl-3-O-[(R)-1-carboxyethyl]-2-deoxy-α-D-glucopyranoside-1-α-(diphenyl phophate) 1',4-lactone
• 英文别名: [(2R,4aS,5R,7R,8R,8aR)-8-acetamido-7-diphenoxyphosphoryloxy-2-methyl-3-oxo-5,7,8,8a-tetrahydro-4aH-pyrano[3,4-b][1,4]dioxin-5-yl]methyl acetate
• CAS: 262853-72-5
• 化学式: C₂₅H₂₈NO₁₁P
• 分子量: 549.471
• InChiKey: SKEDANBYFWDGSW-KZTPRUSUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  38
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  145
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  2-acetamido-6-O-acetyl-3-O-[(R)-1-carboxyethyl]-2-deoxy-α-D-glucopyranoside-1-α-(diphenyl phophate) 1',4-lactone 在 platinum(IV) oxide lithium hydroxide 、 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 生成 N-acetylmuramic acid 1-phosphate α-anomer
  参考文献：
  名称：

  Multi gram synthesis of UDP- N -acetylmuramic acid

  摘要：

  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.

  DOI：

  10.1016/s0960-894x(99)00638-1
• 作为产物：
  描述：

  benzyl 2-acetamido-6-O-acetyl-3-O-<(R)-1-carboxyethyl>-2-deoxy-α-D-glucopyranoside 1',4-lactone 在 palladium on activated charcoal 氢气 、 4-吡咯烷基吡啶 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 2-acetamido-6-O-acetyl-3-O-[(R)-1-carboxyethyl]-2-deoxy-α-D-glucopyranoside-1-α-(diphenyl phophate) 1',4-lactone
  参考文献：
  名称：

  Multi gram synthesis of UDP- N -acetylmuramic acid

  摘要：

  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.

  DOI：

  10.1016/s0960-894x(99)00638-1

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。