6''-β-mercaptoethylether-Boc5-tobramycin | 194785-93-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6''-β-mercaptoethylether-Boc5-tobramycin
• 英文别名: tert-butyl N-[(2S,3R,4S,5S,6S)-3,5-dihydroxy-2-[(1S,2S,3R,4S,6R)-2-hydroxy-3-[(2R,3R,5S,6R)-5-hydroxy-3-[(2-methylpropan-2-yl)oxycarbonylamino]-6-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]oxan-2-yl]oxy-4,6-bis[(2-methylpropan-2-yl)oxycarbonylamino]cyclohexyl]oxy-6-[2-(2-sulfanylethoxy)ethylsulfanylmethyl]oxan-4-yl]carbamate
• CAS: 194785-93-8
• 化学式: C₄₇H₈₅N₅O₁₉S₂
• 分子量: 1088.35
• InChiKey: QWRXJAIPQWXOML-FUVCMGCZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  73
• 可旋转键数：
  27
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  345
• 氢给体数：
  10
• 氢受体数：
  21

反应信息

• 作为反应物：
  描述：

  6''-β-mercaptoethylether-Boc5-tobramycin 在 三异丙基硅烷 、 1,2-乙二硫醇 、 sodium chloride 作用下， 以 二甲基亚砜 、 1,2-二氯乙烷 为溶剂， 反应 2.25h， 生成 amino torba-fluorescein
  参考文献：
  名称：

  [EN] GUANIDINIUM DERIVATIVES FOR IMPROVED CELLULAR TRANSPORT
  [FR] DERIVES DE GUANIDINIUM POUR L'AMELIORATION DU TRANSFERT CELLULAIRE

  摘要：

  公开号：

  WO2005025513A3
• 作为产物：
  描述：

  Boc₅-tobramycin 在 吡啶 、 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 生成 6''-β-mercaptoethylether-Boc5-tobramycin
  参考文献：
  名称：

  [EN] GUANIDINIUM DERIVATIVES FOR IMPROVED CELLULAR TRANSPORT
  [FR] DERIVES DE GUANIDINIUM POUR L'AMELIORATION DU TRANSFERT CELLULAIRE

  摘要：

  公开号：

  WO2005025513A3

文献信息

• Enhanced RNA binding of dimerized aminoglycosides
  作者：Katja Michael、Hai Wang、Yitzhak Tor

  DOI：10.1016/s0968-0896(99)00071-1

  日期：1999.7

  symmetrical and nonsymmetrical dimeric aminoglycosides. These unnatural derivatives were compared to their natural "monomeric" counterparts in their ability to inhibit the Tetrahymena ribozyme. The dimeric aminoglycosides inhibit ribozyme function 20 to 1.2 x 10(3) fold more effectively than their natural parent compounds. The inhibition curves of dimeric aminoglycosides have characteristic shapes suggesting

  氨基糖苷类抗生素最近已成为一个有趣的RNA结合分子家族，它们已成为设计新型RNA配体的主要结构。氨基糖苷-RNA识别现象的去神秘化是开发高级结合剂所必需的。为了探索大RNA分子中多个结合位点的存在，我们合成了共价连接的对称和非对称二聚氨基糖苷。将这些非天然衍生物与它们的天然“单体”对应物在抑制四膜虫核酶方面的能力进行了比较。二聚氨基糖苷比其天然母体化合物更有效地抑制核酶功能20到1.2 x 10（3）倍。二聚氨基糖苷的抑制曲线具有特征性形状，表明在核酶的三维折叠中存在至少两个高亲和力结合位点。提出了二聚氨基糖苷与RNA分子的两个互补位点的相互作用。这种结合基序可能对靶向细菌和病毒病原体的关键RNA分子的新药物的开发有影响。
• Dimeric aminoglycosides: Design, synthesis and RNA binding
  作者：Hai Wang、Yitzhak Tor

  DOI：10.1016/s0960-894x(97)00339-9

  日期：1997.7

  The design and synthesis of symmetrical and non-symmetrical dimeric aminoglycosides derived from kanamycin A, tobramycin, and neomycin B are described. The covalently-linked dimeric aminoglycosides show enhanced activity as ribozyme inhibitors when compared to their natural counterparts. (C) 1997 Elsevier Science Ltd.
• Cellular Uptake of Aminoglycosides, Guanidinoglycosides, and Poly-arginine
  作者：Nathan W. Luedtke、Peter Carmichael、Yitzhak Tor

  DOI：10.1021/ja0360135

  日期：2003.10.1

  Aminoglycosides (including neomycin B and tobramycin) exhibit poor uptake by eukaryotic cell lines. When the amines of these natural products are converted into guanidine groups, their cellular uptake is dramatically enhanced. We have synthesized BODIPY-containing aminoglycosides and guanidinoglycosides to evaluate their cellular uptake properties. Fluorescence activated cell sorting (FACS) and fluorescence microscopy are used to compare the membrane translocation and the cellular localization of these compounds. Upon guanidinylation, the cellular uptake efficiencies of tobramycin and neomycin B are enhanced by 10-fold and 20-fold, respectively. Guanidino-neomycin B exhibits a highly efficient uptake, superior to a fluorescent poly-arginine peptide. Interestingly, the cellular uptake of this common transduction peptide is inhibited by guanidine-neomycin B, suggesting a similar uptake mechanism for both the arginine-rich peptides and the guanidinoglycosides.