Fmoc-L-Dab(Boc-L-Leu-D-Ala-L-Chp)-OBn | 668985-71-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Fmoc-L-Dab(Boc-L-Leu-D-Ala-L-Chp)-OBn
• CAS: 668985-71-5
• 化学式: C₄₈H₅₆ClN₅O₁₀
• 分子量: 898.453
• InChiKey: XELWRHWVPMDVIB-LKKAFCJWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  64.0
• 可旋转键数：
  18.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  210.49
• 氢给体数：
  6.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  Fmoc-L-Dab(Boc-L-Leu-D-Ala-L-Chp)-OBn 在 palladium on activated charcoal N-羟基-7-氮杂苯并三氮唑 、 四丁基氟化铵 、 氢气 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 50.0h， 生成 Fmoc-L-Asn(Trt)-L-Dab(Boc-L-Leu-D-Ala-L-Chp)-OH
  参考文献：
  名称：

  Total Synthesis and Examination of Three Key Analogues of Ramoplanin: A Lipoglycodepsipeptide with Potent Antibiotic Activity

  摘要：

  The total synthesis and evaluation of three key ramoplanin aglycon analogues are detailed. The first (5a) represents replacement of the labile depsipeptide ester with a stable amide (HAsn2 --> Dap2) with removal of the HAsn pendant carboxamide, and it was found to be slightly more potent than the natural aglycon in antimicrobial assays providing a new lead structure with an improved profile and a more stable and accessible macrocyclic template on which to conduct structure-function studies. In contrast, a second amide analogue 5b which contains a single additional methylene relative to 5a (HAsn2 --> Dab2) was found to be inactive in antimicrobial assays (>100-fold loss in activity). The third key analogue 5c in which the Asn1 lipid side chain was replaced with an acetyl group revealed that it contributes significantly to the antimicrobial activity (16-fold) of the ramoplanins, but is not essential.

  DOI：

  10.1021/ja039671y
• 作为产物：
  描述：

  NAlpha-芴甲氧羰基-Nγ-羰-L-2,4-氨基丁酸 在 盐酸 、 碳酸氢钠 、 3-(二乙氧基邻酰氧基)-1,2,3-苯并三嗪-4-酮 作用下， 以 四氢呋喃 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 62.83h， 生成 Fmoc-L-Dab(Boc-L-Leu-D-Ala-L-Chp)-OBn
  参考文献：
  名称：

  Total Synthesis and Examination of Three Key Analogues of Ramoplanin: A Lipoglycodepsipeptide with Potent Antibiotic Activity

  摘要：

  The total synthesis and evaluation of three key ramoplanin aglycon analogues are detailed. The first (5a) represents replacement of the labile depsipeptide ester with a stable amide (HAsn2 --> Dap2) with removal of the HAsn pendant carboxamide, and it was found to be slightly more potent than the natural aglycon in antimicrobial assays providing a new lead structure with an improved profile and a more stable and accessible macrocyclic template on which to conduct structure-function studies. In contrast, a second amide analogue 5b which contains a single additional methylene relative to 5a (HAsn2 --> Dab2) was found to be inactive in antimicrobial assays (>100-fold loss in activity). The third key analogue 5c in which the Asn1 lipid side chain was replaced with an acetyl group revealed that it contributes significantly to the antimicrobial activity (16-fold) of the ramoplanins, but is not essential.

  DOI：

  10.1021/ja039671y