1-O-methyl-6-O-((3R)-3,4-dihydroxy-2-methylenebutanoyl)-α-D-glucopyranose | 1222854-63-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 糖脂
• 英文名称: 1-O-methyl-6-O-((3R)-3,4-dihydroxy-2-methylenebutanoyl)-α-D-glucopyranose
• 英文别名: 1-O-methyl-α-epi-6-tuliposide B；[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-methoxyoxan-2-yl]methyl (3R)-3,4-dihydroxy-2-methylidenebutanoate
• CAS: 1222854-63-8
• 化学式: C₁₂H₂₀O₉
• 分子量: 308.285
• InChiKey: DLQSNOKYUUMSHR-BZKDFATFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  146
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  1-O-methyl-6-O-[(3R)-3-(tert-butyldimethylsilyloxy)-4-(p-methoxybenzyloxy)-2-methylenebutanoyl]-2,3,4-tri-O-trimethylsilyl-α-D-glucopyranose 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 1-O-methyl-6-O-((3R)-3,4-dihydroxy-2-methylenebutanoyl)-α-D-glucopyranose
  参考文献：
  名称：

  The antibacterial properties of 6-tuliposide B. Synthesis of 6-tuliposide B analogues and structure–activity relationship

  摘要：

  6-Tuliposide B is a secondary metabolite occurring specifically in tulip anthers. Recently, a potent antibacterial activity of 6-tuliposide B has been reported. However, its molecular target has not yet been established, nor its action mechanism. To shed light on such issues, 6-tuliposide B and tulipalin B analogues were synthesized and a structure-activity relationship (SAR) was examined using a broad panel of bacterial strains. As the results of SAR among a total of 25 compounds, only tulipalin B and the compounds having 3',4'-dihydroxy-2'-methylenebutanoate (DHMB) moieties showed any significant antibacterial activity. Moreover, the 3'R analogues of these compounds displayed essentially the same activities as 6-tuliposide B and the structure of the 3'R-DMBA moiety was the same as that of the proposed active moiety of cnicin. These results suggest that 6-tuliposide B has the same action mechanism as proposed for cnicin and bacteria) MurA is one of the major molecular targets of 6-tuliposide B. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2009.10.008

文献信息

• The antibacterial properties of 6-tuliposide B. Synthesis of 6-tuliposide B analogues and structure–activity relationship
  作者：Kengo Shigetomi、Kazuaki Shoji、Shinya Mitsuhashi、Makoto Ubukata

  DOI：10.1016/j.phytochem.2009.10.008

  日期：2010.2

  6-Tuliposide B is a secondary metabolite occurring specifically in tulip anthers. Recently, a potent antibacterial activity of 6-tuliposide B has been reported. However, its molecular target has not yet been established, nor its action mechanism. To shed light on such issues, 6-tuliposide B and tulipalin B analogues were synthesized and a structure-activity relationship (SAR) was examined using a broad panel of bacterial strains. As the results of SAR among a total of 25 compounds, only tulipalin B and the compounds having 3',4'-dihydroxy-2'-methylenebutanoate (DHMB) moieties showed any significant antibacterial activity. Moreover, the 3'R analogues of these compounds displayed essentially the same activities as 6-tuliposide B and the structure of the 3'R-DMBA moiety was the same as that of the proposed active moiety of cnicin. These results suggest that 6-tuliposide B has the same action mechanism as proposed for cnicin and bacteria) MurA is one of the major molecular targets of 6-tuliposide B. (C) 2009 Elsevier Ltd. All rights reserved.