(Bis-N,N'-(Cbz)-L-lysyl-D-threo-β-hydroxyaspartyl β-benzyl ester)-L-alanyl-D-allo-threonyl-L-alanyl-δ-N-(benzyloxy)-D-cycloornithine | 162553-90-4

• 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: (Bis-N,N'-(Cbz)-L-lysyl-D-threo-β-hydroxyaspartyl β-benzyl ester)-L-alanyl-D-allo-threonyl-L-alanyl-δ-N-(benzyloxy)-D-cycloornithine
• 英文别名: benzyl (2R,3R)-3-[[(2S)-2,6-bis(phenylmethoxycarbonylamino)hexanoyl]amino]-2-hydroxy-4-[[(2S)-1-[[(2R,3R)-3-hydroxy-1-oxo-1-[[(2S)-1-oxo-1-[[(3R)-2-oxo-1-phenylmethoxypiperidin-3-yl]amino]propan-2-yl]amino]butan-2-yl]amino]-1-oxopropan-2-yl]amino]-4-oxobutanoate
• CAS: 162553-90-4
• 化学式: C₅₅H₆₈N₈O₁₅
• 分子量: 1081.19
• InChiKey: QGRMXTFZRTVTLY-FSPRFFIXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  78
• 可旋转键数：
  31
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  319
• 氢给体数：
  9
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  (Bis-N,N'-(Cbz)-L-lysyl-D-threo-β-hydroxyaspartyl β-benzyl ester)-L-alanyl-D-allo-threonyl-L-alanyl-δ-N-(benzyloxy)-D-cycloornithine 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以100%的产率得到L-Lysyl-D-threo-β-(hydroxyaspartyl)-L-alanyl-D-allo-threonyl-L-alanyl-δ-N-hydroxy-D-cycloornithine
  参考文献：
  名称：

  Synthesis of the Peptide Fragment of Pseudobactin

  摘要：

  Synthesis of the peptide fragment, L-Lys-D-threo-beta-OH-Asp-L-Ala-D-allo-Thr-L-Ala-N-OH-D-cOrn, of pseudobactin (2) is reported. By utilizing 2-ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinoline (EEDQ) as a coupling reagent, peptide bonds were constructed without requiring protection of hydroxyl groups. To access the D-allo-Thr residue in the peptide fragment of pseudobactin, the Thr residue in N-Cbz-L-Ala-D-Thr-L-Ala . O-t-Bu (4b) was converted to a peptidyl oxazoline using Burgess' reagent. Hydrolysis of the oxazoline with 1 N HCl followed by base-catalyzed acyl migration then provided the D-allo-Thr analog 4a.

  DOI：

  10.1021/jo00112a009
• 作为产物：
  描述：

  N,N’-双苄氧羰基-L-赖氨酸 在 potassium hydrogencarbonate 、 2-乙氧基-1-乙氧碳酰基-1,2-二氢喹啉 、 三乙胺 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 氯仿 、 水 为溶剂， 反应 95.0h， 生成 (Bis-N,N'-(Cbz)-L-lysyl-D-threo-β-hydroxyaspartyl β-benzyl ester)-L-alanyl-D-allo-threonyl-L-alanyl-δ-N-(benzyloxy)-D-cycloornithine
  参考文献：
  名称：

  Synthesis of the Peptide Fragment of Pseudobactin

  摘要：

  Synthesis of the peptide fragment, L-Lys-D-threo-beta-OH-Asp-L-Ala-D-allo-Thr-L-Ala-N-OH-D-cOrn, of pseudobactin (2) is reported. By utilizing 2-ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinoline (EEDQ) as a coupling reagent, peptide bonds were constructed without requiring protection of hydroxyl groups. To access the D-allo-Thr residue in the peptide fragment of pseudobactin, the Thr residue in N-Cbz-L-Ala-D-Thr-L-Ala . O-t-Bu (4b) was converted to a peptidyl oxazoline using Burgess' reagent. Hydrolysis of the oxazoline with 1 N HCl followed by base-catalyzed acyl migration then provided the D-allo-Thr analog 4a.

  DOI：

  10.1021/jo00112a009

文献信息

• Synthesis of the Peptide Fragment of Pseudobactin
  作者：John F. Okonya、Teodozyj Kolasa、Marvin J. Miller

  DOI：10.1021/jo00112a009

  日期：1995.4

  Synthesis of the peptide fragment, L-Lys-D-threo-beta-OH-Asp-L-Ala-D-allo-Thr-L-Ala-N-OH-D-cOrn, of pseudobactin (2) is reported. By utilizing 2-ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinoline (EEDQ) as a coupling reagent, peptide bonds were constructed without requiring protection of hydroxyl groups. To access the D-allo-Thr residue in the peptide fragment of pseudobactin, the Thr residue in N-Cbz-L-Ala-D-Thr-L-Ala . O-t-Bu (4b) was converted to a peptidyl oxazoline using Burgess' reagent. Hydrolysis of the oxazoline with 1 N HCl followed by base-catalyzed acyl migration then provided the D-allo-Thr analog 4a.