N-[4(R)-(tert-butyloxycarbonyl)amino-3(S)-hydroxy-2(S)-methylpentanoyl]-N-methyl-L-threonine methyl ester | 197146-88-6

• 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: N-[4(R)-(tert-butyloxycarbonyl)amino-3(S)-hydroxy-2(S)-methylpentanoyl]-N-methyl-L-threonine methyl ester
• CAS: 197146-88-6
• 化学式: C₁₇H₃₂N₂O₇
• 分子量: 376.45
• InChiKey: BFQXNQQMBJXQEV-QWQWKMKNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.28
• 重原子数：
  26.0
• 可旋转键数：
  7.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  125.4
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  N-[4(R)-(tert-butyloxycarbonyl)amino-3(S)-hydroxy-2(S)-methylpentanoyl]-N-methyl-L-threonine methyl ester 在 lithium hydroxide 作用下， 以 叔丁醇 为溶剂， 反应 0.5h， 以86%的产率得到N-[4(R)-(tert-butyloxycarbonyl)amino-3(S)-hydroxy-2(S)-methylpentanoyl]-N-methylthreonine
  参考文献：
  名称：

  N-methyl threonine analogues of deglycobleomycin A2: Synthesis and evaluation

  摘要：

  The synthesis of 5 and its D-allo-threonine epimer 6 and the comparison of their DNA cleavage efficiency and selectivity with that of deglycobleomycin A(2) (3) are detailed. The studies illustrate that N-methylation of the L-threonine subunit within deglycobleomycin A(2) dramatically reduces the DNA cleavage efficiency (10-15-fold), weakens and nearly abolishes the inherent DNA cleavage selectivity, but has little effect on the inherent oxidation capabilities of the activated Fe(III) complexes. The results are consistent with a previously unrecognized prominent role for the threonine NH and the potential importance of a hydrogen bond to the Fe(III) hydroperoxide complex of bleomycin or a subsequent activated complex implicated in recent structural models. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(97)00107-7
• 作为产物：
  描述：

  (4R,5S)-5-((S)-1-Carboxy-ethyl)-4-methyl-2-phenyl-oxazolidine-3-carboxylic acid tert-butyl ester 在 palladium on activated charcoal 氢气 、 1-羟基苯并三唑 、 溶剂黄146 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 25.0~60.0 ℃ 、101.33 kPa 条件下， 反应 16.0h， 生成 N-[4(R)-(tert-butyloxycarbonyl)amino-3(S)-hydroxy-2(S)-methylpentanoyl]-N-methyl-L-threonine methyl ester
  参考文献：
  名称：

  N-methyl threonine analogues of deglycobleomycin A2: Synthesis and evaluation

  摘要：

  The synthesis of 5 and its D-allo-threonine epimer 6 and the comparison of their DNA cleavage efficiency and selectivity with that of deglycobleomycin A(2) (3) are detailed. The studies illustrate that N-methylation of the L-threonine subunit within deglycobleomycin A(2) dramatically reduces the DNA cleavage efficiency (10-15-fold), weakens and nearly abolishes the inherent DNA cleavage selectivity, but has little effect on the inherent oxidation capabilities of the activated Fe(III) complexes. The results are consistent with a previously unrecognized prominent role for the threonine NH and the potential importance of a hydrogen bond to the Fe(III) hydroperoxide complex of bleomycin or a subsequent activated complex implicated in recent structural models. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(97)00107-7