N'-dodecyl-(2R)-2-(tert-butoxycarbonylamino)-2-[6-deoxy-6-(t-butoxycarbonylamino)-β-D-glucopyranosyl]ethanamide | 1292804-49-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N'-dodecyl-(2R)-2-(tert-butoxycarbonylamino)-2-[6-deoxy-6-(t-butoxycarbonylamino)-β-D-glucopyranosyl]ethanamide
• CAS: 1292804-49-9
• 化学式: C₃₀H₅₇N₃O₉
• 分子量: 603.797
• InChiKey: UAEZRTLCZYJGHC-QRCODTGVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.29
• 重原子数：
  42.0
• 可旋转键数：
  16.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  175.68
• 氢给体数：
  6.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  N'-dodecyl-(2R)-2-(tert-butoxycarbonylamino)-2-[6-deoxy-6-(t-butoxycarbonylamino)-β-D-glucopyranosyl]ethanamide 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 生成 N'-dodecyl-[[(2R)-2-guanidinyl-2-]-(6-guanidinyl-6-deoxy)-b-D-glucopyranosyl]ethanamide*2 trifluoroacetic acid
  参考文献：
  名称：

  Synthesis and antibacterial properties of carbohydrate-templated lysine surfactants

  摘要：

  The synthesis of four dicationic glucose-templated D-lysine-derived surfactants and their two unmodified D-lysine-analogs is described. Replacement of D-lysine by D-glucose-templated-D-lysine provides a general tool to introduce chemical diversity into the side chain of lysine. The presence of the polyfunctional D-gluco-configured polyol scaffold provides rich opportunities to study structure-activity relationships in lysine-lipid conjugates. All cationic lipids were tested for inhibition of bacterial growth using a panel of clinically relevant Gram-positive and Gram-negative strains. Our results show that substitution of D-lysine by D-glucose-templated D-lysine surfactants retains, but does not improve, the antibacterial activity. Similarly, conversion of the D-gluco-based polyol scaffold into a hydrophobically enhanced tri-O-phenylcarbamate scaffold does not further enhance the antibacterial activity of the cationic lipid. However, improvements in the antibacterial activity were observed by guanidinylation of the two lysine-based amino groups. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.01.025
• 作为产物：
  描述：

  十二烷基伯胺 、 (2R)-2-(t-butoxycarbonylamino)-2-[6-deoxy-6-(t-butoxycarbonylamino)-β-D-glucopyranosyl]-ethanoic acid 在 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 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 2.0h， 以92%的产率得到N'-dodecyl-(2R)-2-(tert-butoxycarbonylamino)-2-[6-deoxy-6-(t-butoxycarbonylamino)-β-D-glucopyranosyl]ethanamide
  参考文献：
  名称：

  Synthesis and antibacterial properties of carbohydrate-templated lysine surfactants

  摘要：

  The synthesis of four dicationic glucose-templated D-lysine-derived surfactants and their two unmodified D-lysine-analogs is described. Replacement of D-lysine by D-glucose-templated-D-lysine provides a general tool to introduce chemical diversity into the side chain of lysine. The presence of the polyfunctional D-gluco-configured polyol scaffold provides rich opportunities to study structure-activity relationships in lysine-lipid conjugates. All cationic lipids were tested for inhibition of bacterial growth using a panel of clinically relevant Gram-positive and Gram-negative strains. Our results show that substitution of D-lysine by D-glucose-templated D-lysine surfactants retains, but does not improve, the antibacterial activity. Similarly, conversion of the D-gluco-based polyol scaffold into a hydrophobically enhanced tri-O-phenylcarbamate scaffold does not further enhance the antibacterial activity of the cationic lipid. However, improvements in the antibacterial activity were observed by guanidinylation of the two lysine-based amino groups. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.01.025