Z-Phe-NCO | 112037-34-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Z-Phe-NCO
• 英文别名: benzyl N-[(1R)-1-isocyanato-2-phenylethyl]carbamate
• CAS: 112037-34-0；88425-14-3
• 化学式: C₁₇H₁₆N₂O₃
• 分子量: 296.326
• InChiKey: LYKXXSOVBCACLU-INIZCTEOSA-N

物化性质

• 沸点：
  465.3±45.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  67.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Z-Phe-NCO 在 钯 氢气 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 21.0h， 生成 H-Phe-Φ(NHCONH)-Leu-OH
  参考文献：
  名称：

  Amino acids and peptides. IX. Synthetic studies on Leu-enkephalin analogues containing a ureylene bond.

  摘要：

  我们合成了含有脲键而非酰胺键的亮烯酮类似物。脲烯键是由相应叠氮化物中的异氰酸酯通过库尔提斯重排反应偶联生成的。制备了三种类似物，每种都在 Tyr-Gly、Gly-Gly 或 Phe-Leu 酰胺键上有一个脲烯键。脲烯键可抗酶水解，但合成肽在豚鼠回肠和小鼠输精管上的生物活性低于Leu-enkephalin。

  DOI：

  10.1248/cpb.36.1766
• 作为产物：
  描述：

  N-苄氧羰基-L-苯丙氨酰胺 在 吡啶 、 [双(三氟乙酰氧基)碘]苯 作用下， 以 四氢呋喃 为溶剂， 生成 Z-Phe-NCO
  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

文献信息

• Carbonyldiimidazole (CDI) Mediated Synthesis of Nα-Protected Amino Acid Azides: Application to the One-pot Preparation of Ureidopeptides
  作者：B. Vasantha、T. M. Vishwanatha、Vommina V. Sureshbabu

  DOI：10.2174/092986611797200922

  日期：2011.11.1

  Synthesis of Nα-protected amino acyl azides starting from corresponding acids via the carbonyldiimidazole (CDI) activation is described. The protocol is extended for a one-pot preparation of ureido peptides that circumvents the isolation of acyl azide and isocyanate intermediates. The reaction was accomplished without using any additives and base. The protocol is simple, clean, high yielding and free

  描述了通过羰基二咪唑（CDI）活化从相应的酸开始合成Nα-保护的氨基酰基叠氮化物。该协议扩展为一锅式制备脲基肽，可避免酰基叠氮化物和异氰酸酯中间体的分离。不使用任何添加剂和碱即可完成反应。该方案简单，清洁，高收率且无消旋作用。
• Succinimidyl Carbamate Derivatives fromN-Protected α-Amino Acids and Dipeptides―Synthesis of Ureidopeptides and Oligourea/Peptide Hybrids
  作者：Lucile Fischer、Vincent Semetey、Jose-Manuel Lozano、Arnaud-Pierre Schaffner、Jean-Paul Briand、Claude Didierjean、Gilles Guichard

  DOI：10.1002/ejoc.200601010

  日期：2007.5

  direct precursors of 1,3,5-triazepan-2,6-diones, a novel class of conformationally constrained dipeptide mimetics. Herein, we have evaluated the use of these building blocks for the synthesis of ureido-peptides (in solution and on solid support), peptidyl hydantoins, oligoureas and some oligo(urea/amide) hybrids. Conformational investigations by NMR of ureidotripeptide 6i and pentamer 10, consisting of alternating

  由多种N制备琥珀酰亚胺（1-[（烷氧基）羰基]氨基}-1-X-甲基）氨基甲酸酯（4）和琥珀酰亚胺[1-（酰氨基）-1-X-甲基]氨基甲酸酯（5）描述了 -Boc-、-Z- 或 -Fmoc 保护的 α-氨基酸和二肽以及氨基甲酸酯的结构特征。我们之前已经表明，源自 N-Boc 二肽的琥珀酰亚胺氨基甲酸酯 5 可以作为 1,3,5-三氮杂-2,6-二酮（一类新型的构象受限二肽模拟物）的直接前体。在此，我们评估了这些构件在合成脲基肽（在溶液中和在固体支持物上）、肽基乙内酰脲、低聚脲和一些低聚（脲/酰胺）杂化物的用途。脲基三肽 6i 和五聚体 10 的 NMR 构象研究，由交替的酰胺和脲组成，建议折叠构象（即尿素转向）以尿素键的顺，反（E，Z）几何形状为特征，填充在 [D5] 吡啶和 [D6] DMSO 溶液中。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim
• Synthesis of <i>N</i> ^{<font>α</font>}-Protected Amino Acid–Derived Selenocarbamates Employing Isocyanates as Key Intermediates
  作者：Vommina V. Sureshbabu、Shankar A. Naik

  DOI：10.1080/00397910903318641

  日期：2010.8.16

  A simple protocol for the synthesis of N-urethane-protected N-alkyl-Se-alkyl selenocarbamate derivatives of amino acids has been described. The reaction of N-urethane-protected amino alkyl isocyanates with selenating agent LiAlHSeH and subsequent coupling with an alkyl halide yielded the title compounds in good yield and purity. All the selenocarbamates obtained have been characterized by 1H NMR, 13C NMR, and mass spectral studies.
• Facile incorporation of urea pseudopeptides into protease substrate analogue inhibitors
  作者：Adam C. Myers、Jennifer A. Kowalski、Mark A. Lipton

  DOI：10.1016/j.bmcl.2004.07.092

  日期：2004.10

  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.
• Amino acids and peptides. IX. Synthetic studies on Leu-enkephalin analogues containing a ureylene bond.
  作者：KOICHI KAWASAKI、MITSUKO MAEDA、JOE WATANABE、HIROSHI KANETO

  DOI：10.1248/cpb.36.1766

  日期：——

  Leu-enkephalin analogues containing a ureylene bond instead of an amide bond were synthesized. The ureylene bond was formed by a coupling reaction of the isocyanate derived from the corresponding azide by Curtius rearrangement reaction. Three analogues, each of which has a ureylene bond at the Tyr-Gly or Gly-Gly or Phe-Leu amide bond, were prepared. The ureylene bond resisted enzymatic hydrolysis, but the biological activities of the synthetic peptides on guinea pig ileum and mouse was deferens were low compared with those of Leu-enkephalin.

  我们合成了含有脲键而非酰胺键的亮烯酮类似物。脲烯键是由相应叠氮化物中的异氰酸酯通过库尔提斯重排反应偶联生成的。制备了三种类似物，每种都在 Tyr-Gly、Gly-Gly 或 Phe-Leu 酰胺键上有一个脲烯键。脲烯键可抗酶水解，但合成肽在豚鼠回肠和小鼠输精管上的生物活性低于Leu-enkephalin。