(2R,3R)-2-ethoxycarboxyaziridine-3-carboxyl-Leu-(3S,4S)-4-amino-3-hydroxy-6-methylheptanoyl-(S)-α-aminobutyric acid | 952065-33-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: (2R,3R)-2-ethoxycarboxyaziridine-3-carboxyl-Leu-(3S,4S)-4-amino-3-hydroxy-6-methylheptanoyl-(S)-α-aminobutyric acid
• 英文别名: H-D-Azi(CO2Et)(CO2Et)-Leu-Sta-Abu-OH；(2S)-2-[[(3S,4S)-4-[[(2S)-2-[[(2R,3R)-3-ethoxycarbonylaziridine-2-carbonyl]amino]-4-methylpentanoyl]amino]-3-hydroxy-6-methylheptanoyl]amino]butanoic acid
• CAS: 952065-33-7
• 化学式: C₂₄H₄₂N₄O₈
• 分子量: 514.619
• InChiKey: VTCXCKTZSFQNNN-LXJANLPBSA-N

物化性质

• 沸点：
  817.8±65.0 °C(Predicted)
• 密度：
  1.195±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  36
• 可旋转键数：
  17
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  193
• 氢给体数：
  6
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (2R,3R)-2-ethoxycarboxyaziridine-3-carboxyl-Leu-(3S,4S)-4-amino-3-hydroxy-6-methylheptanoyl-(S)-α-aminobutyric acid 在 porcine liver esterase 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 132.0h， 以79%的产率得到(2R,3R)-3-carboxyaziridin-2-yl-carbonyl-Leu-(3S,4S)-4-amino-3-hydroxy-6-methylheptanoyl-(S)-α-aminobutyric acid
  参考文献：
  名称：

  Total synthesis of miraziridine A and identification of its major reaction site for cathepsin B

  摘要：

  The synthesis of miraziridine A, a pentapeptide derivative isolated from marine sponge, and its truncated analogs has been achieved. To construct the backbone of miraziridine A, a side-chain-unprotected vinylogous arginine was condensed with an aziridine-containing fragment prepared by a conventional solid-phase procedure. An analog lacking the vinylogous arginine site showed comparable inhibitory activity with miraziridine A, whereas an analog lacking the aziridine site showed remarkably weak inhibitory activity for cathepsin B. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.06.082
• 作为产物：
  描述：

  Boc-(3R,4S)-statine ethyl ester 在 lithium hydroxide 、 甲基磺酰氯 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 4.75h， 生成 (2R,3R)-2-ethoxycarboxyaziridine-3-carboxyl-Leu-(3S,4S)-4-amino-3-hydroxy-6-methylheptanoyl-(S)-α-aminobutyric acid
  参考文献：
  名称：

  Total synthesis of miraziridine A and identification of its major reaction site for cathepsin B

  摘要：

  The synthesis of miraziridine A, a pentapeptide derivative isolated from marine sponge, and its truncated analogs has been achieved. To construct the backbone of miraziridine A, a side-chain-unprotected vinylogous arginine was condensed with an aziridine-containing fragment prepared by a conventional solid-phase procedure. An analog lacking the vinylogous arginine site showed comparable inhibitory activity with miraziridine A, whereas an analog lacking the aziridine site showed remarkably weak inhibitory activity for cathepsin B. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.06.082