(S)-2-{(S)-2-[3-({2-[(S)-2-Benzyloxycarbonylamino-3-(4-benzyloxy-phenyl)-propionylamino]-acetylamino}-methyl)-ureido]-3-phenyl-propionylamino}-4-methyl-pentanoic acid benzyl ester | 241154-53-0

• 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: (S)-2-{(S)-2-[3-({2-[(S)-2-Benzyloxycarbonylamino-3-(4-benzyloxy-phenyl)-propionylamino]-acetylamino}-methyl)-ureido]-3-phenyl-propionylamino}-4-methyl-pentanoic acid benzyl ester
• CAS: 241154-53-0
• 化学式: C₅₀H₅₆N₆O₉
• 分子量: 885.029
• InChiKey: DHLPAXURQKJDPE-KJFLPAQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.48
• 重原子数：
  65.0
• 可旋转键数：
  23.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  202.29
• 氢给体数：
  6.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (S)-2-{(S)-2-[3-({2-[(S)-2-Benzyloxycarbonylamino-3-(4-benzyloxy-phenyl)-propionylamino]-acetylamino}-methyl)-ureido]-3-phenyl-propionylamino}-4-methyl-pentanoic acid benzyl ester 在 palladium dihydroxide 氢气 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 4.0h， 以79%的产率得到Tyr-Gly-Gly-ψ(NH-CO-NH)-Phe-Leu-OH
  参考文献：
  名称：

  Facile incorporation of urea pseudopeptides into protease substrate analogue inhibitors

  摘要：

  A new procedure that employs a one-pot, oxidative Hofmann rearrangement to incorporate a urea linkage into peptide backbones is detailed herein. This methodology was used to replace the scissile peptide bonds of [Leu(5)]enkephalin and a hexapeptide HIV-1 protease substrate. The [Leu(5)]enkephalin analogue was found to inhibit cleavage of hippurylhistidylleucine (HHL) by porcine kidney angiotensin-converting enzyme (PK-ACE) with a 0.88 mM IC50 value, comparable to the Michaelis constant of [Leu(5)]enkephalin with the same enzyme. The HIV-1 protease substrate analogue was shown to inhibit HIV-1 protease with an IC50 = 34muM. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.07.092
• 作为产物：
  描述：

  Z-Tyr(OBn)-Gly-Gly-NH2 在 吡啶 、 N,N-二异丙基乙胺 、 [双(三氟乙酰氧基)碘]苯 作用下， 以 四氢呋喃 为溶剂， 反应 17.0h， 生成 (S)-2-{(S)-2-[3-({2-[(S)-2-Benzyloxycarbonylamino-3-(4-benzyloxy-phenyl)-propionylamino]-acetylamino}-methyl)-ureido]-3-phenyl-propionylamino}-4-methyl-pentanoic acid benzyl ester
  参考文献：
  名称：

  Facile incorporation of urea pseudopeptides into protease substrate analogue inhibitors

  摘要：

  A new procedure that employs a one-pot, oxidative Hofmann rearrangement to incorporate a urea linkage into peptide backbones is detailed herein. This methodology was used to replace the scissile peptide bonds of [Leu(5)]enkephalin and a hexapeptide HIV-1 protease substrate. The [Leu(5)]enkephalin analogue was found to inhibit cleavage of hippurylhistidylleucine (HHL) by porcine kidney angiotensin-converting enzyme (PK-ACE) with a 0.88 mM IC50 value, comparable to the Michaelis constant of [Leu(5)]enkephalin with the same enzyme. The HIV-1 protease substrate analogue was shown to inhibit HIV-1 protease with an IC50 = 34muM. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.07.092