(2S,5R)-5-((S)-2,6-Bis-tert-butoxycarbonylamino-hexanoylamino)-2-methyl-4-oxo-hexanoic acid benzyl ester | 593278-49-0

• 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: (2S,5R)-5-((S)-2,6-Bis-tert-butoxycarbonylamino-hexanoylamino)-2-methyl-4-oxo-hexanoic acid benzyl ester
• CAS: 593278-49-0
• 化学式: C₃₀H₄₇N₃O₈
• 分子量: 577.718
• InChiKey: OSJKZDTXKYPCHU-XJUOHMSHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.42
• 重原子数：
  41.0
• 可旋转键数：
  14.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  149.13
• 氢给体数：
  3.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (2S,5R)-5-((S)-2,6-Bis-tert-butoxycarbonylamino-hexanoylamino)-2-methyl-4-oxo-hexanoic acid benzyl ester 在 palladium on activated charcoal 吡啶 、 氢气 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 4.33h， 生成 (2S,5R)-5-((S)-2,6-Bis-acetylamino-hexanoylamino)-2-methyl-4-oxo-hexanoic acid
  参考文献：
  名称：

  Partitioning the Loss in Vancomycin Binding Affinity for d-Ala-d-Lac into Lost H-Bond and Repulsive Lone Pair Contributions

  摘要：

  The binding affinity of 4, which incorporates a methylene (CH2) in place of the key linking amide of Ac2-l-Lys-d-Ala-d-Ala, for vancomycin was compared with that of Ac2-l-Lys-d-Ala-d-Ala (3) and Ac2-l-Lys-d-Ala-d-Lac (5). The vancomycin affinity for 4 was approximately 10-fold less than that of 3, but 100-fold greater than that of 5. This suggests that the reduced binding affinity of 5 (4.1 kcal/mol) may be attributed to both the loss of a key H-bond (1.5 kcal/mol) and a destabilizing lone pair/lone pair electrostatic interaction introduced with the ester oxygen of 5 (2.6 kcal/mol) with the latter, not the H-bond, being responsible for the largest share of the 1000-fold reduction.

  DOI：

  10.1021/ja035901x
• 作为产物：
  描述：

  (2S,5R)-5-tert-Butoxycarbonylamino-2-methyl-4-oxo-hexanoic acid benzyl ester 在 碳酸氢钠 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 盐酸 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.25h， 生成 (2S,5R)-5-((S)-2,6-Bis-tert-butoxycarbonylamino-hexanoylamino)-2-methyl-4-oxo-hexanoic acid benzyl ester
  参考文献：
  名称：

  Partitioning the Loss in Vancomycin Binding Affinity for d-Ala-d-Lac into Lost H-Bond and Repulsive Lone Pair Contributions

  摘要：

  The binding affinity of 4, which incorporates a methylene (CH2) in place of the key linking amide of Ac2-l-Lys-d-Ala-d-Ala, for vancomycin was compared with that of Ac2-l-Lys-d-Ala-d-Ala (3) and Ac2-l-Lys-d-Ala-d-Lac (5). The vancomycin affinity for 4 was approximately 10-fold less than that of 3, but 100-fold greater than that of 5. This suggests that the reduced binding affinity of 5 (4.1 kcal/mol) may be attributed to both the loss of a key H-bond (1.5 kcal/mol) and a destabilizing lone pair/lone pair electrostatic interaction introduced with the ester oxygen of 5 (2.6 kcal/mol) with the latter, not the H-bond, being responsible for the largest share of the 1000-fold reduction.

  DOI：

  10.1021/ja035901x