2-acetamido-3-O-[(1R)-1-carboxyethyl]-1,2,5-trideoxy-1,5-imino-D-glucitol hydrochloride | 1356848-50-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 2-acetamido-3-O-[(1R)-1-carboxyethyl]-1,2,5-trideoxy-1,5-imino-D-glucitol hydrochloride
• 英文别名: (2R)-2-[(2R,3R,4R,5S)-5-acetamido-3-hydroxy-2-(hydroxymethyl)piperidin-4-yl]oxypropanoic acid;hydrochloride
• CAS: 1356848-50-4
• 化学式: C₁₁H₂₀N₂O₆*ClH
• 分子量: 312.751
• InChiKey: ZEYCQWMDZGANTF-QTDUYKOVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  128
• 氢给体数：
  6
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  在 吡啶 、 盐酸 、 palladium 10% on activated carbon 、 四丁基氟化铵 、 氢气 、 dimethyl sulfide borane 、 sodium hydride 、 sodium cyanoborohydride 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 异丙醇 、 乙腈 、 oil 为溶剂， 反应 64.5h， 生成 2-acetamido-3-O-[(1R)-1-carboxyethyl]-1,2,5-trideoxy-1,5-imino-D-glucitol hydrochloride
  参考文献：
  名称：

  Inhibitors for Bacterial Cell-Wall Recycling

  摘要：

  Gram-negative bacteria have evolved an elaborate process for the recycling of their cell wall, which is initiated in the periplasmic space by the action of lytic transglycosylases. The product of this reaction, beta-D-N-acetylglucosamine-(1 -> 44)-1,6-anhydro-beta-D-N-acetylmuramyl-L-Ala-gamma-D-Glu-meso-DAP-D-Ala-D-Ala (compound 1), is internalized to begin the recycling events within the cytoplasm. The first step in the cytoplasmic recycling is catalyzed by the NagZ glycosylase, which cleaves in a hydrolytic reaction the N-acetylglucosamine glycosidic bond of metabolite 1. The reactions catalyzed by both the lytic glycosylases and NagZ are believed to involve oxocarbenium transition species. We describe herein the synthesis and evaluation of four iminosaccharides as possible mimetics of the oxocarbenium species, and we disclose one as a potent (compound 3, K-i = 300 +/- 15 nM) competitive inhibitor of NagZ.

  DOI：

  10.1021/ml2002746