Alloc-Tyr(t-Bu)-OH

• 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: Alloc-Tyr(t-Bu)-OH
• 英文别名: Alloc-L-tyrosine(OtBu)-OH；(2S)-3-[4-[(2-methylpropan-2-yl)oxy]phenyl]-2-(prop-2-enoxycarbonylamino)propanoic acid
• 化学式: C₁₇H₂₃NO₅
• 分子量: 321.373
• InChiKey: LHCGMTPKPBFNMM-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  三氟乙酸五氟苯酯 、 Alloc-Tyr(t-Bu)-OH 在 吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 Alloc-Tyr(t-Bu)-OPfp
  参考文献：
  名称：

  Nα-Alloc temporary protection in solid-phase peptide synthesis. The use of amine–borane complexes as allyl group scavengers

  摘要：

  使用胺-硼烷复合物与可溶性钯催化剂的组合，可以在接近中性条件下快速去保护烯丙基氨基甲酸酯，且不会产生任何副产物烯丙胺。初步实验表明，钯催化剂-胺-硼烷系统似乎非常适合在固相肽合成中根据Nα-烯丙氧羰基临时保护策略去除Nα-烯丙氧羰基末端基团。

  DOI：

  10.1039/a906025a
• 作为产物：
  描述：

  O-叔丁基-L-酪氨酸 、 氯甲酸烯丙酯 在 sodium hydroxide 、 盐酸 作用下， 以 水 为溶剂， 以70%的产率得到Alloc-Tyr(t-Bu)-OH
  参考文献：
  名称：

  Rational conversion of noncontinuous active region in proteins into a small orally bioavailable macrocyclic drug-like molecule: The HIV-1 CD4:gp120 paradigm

  摘要：

  Rational conversion of noncontinuous active regions of proteins into a small orally bioavailable molecule is crucial for the discovery of new drugs based on inhibition of protein-protein interactions. We developed a method that utilizes backbone cyclization as an intermediate step for conversion of the CD4 noncontinuous active region into small macrocyclic molecules. We demonstrate that this method is feasible by preparing small inhibitor for human immunodeficiency virus infection. The lead compound, CG-1, proved orally available in the rat model. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.04.053

文献信息

• Nα-Alloc temporary protection in solid-phase peptide synthesis. The use of amine–borane complexes as allyl group scavengers
  作者：Paloma Gomez-Martinez、Michèle Dessolin、François Guibé、Fernando Albericio

  DOI：10.1039/a906025a

  日期：——

  The use of a combination of amine–borane complexes and soluble palladium catalyst allows the fast deprotection of allyl carbamates under near-to-neutral conditions and without any side-formation of allylamine. Preliminary experiments indicate that palladium catalyst–amine–borane systems seem ideally suited for removal of Nα-Alloc terminal groups during solid phase peptide synthesis according to the N α-Alloc temporary protection strategy.

  使用胺-硼烷复合物与可溶性钯催化剂的组合，可以在接近中性条件下快速去保护烯丙基氨基甲酸酯，且不会产生任何副产物烯丙胺。初步实验表明，钯催化剂-胺-硼烷系统似乎非常适合在固相肽合成中根据Nα-烯丙氧羰基临时保护策略去除Nα-烯丙氧羰基末端基团。
• Rational conversion of noncontinuous active region in proteins into a small orally bioavailable macrocyclic drug-like molecule: The HIV-1 CD4:gp120 paradigm
  作者：Mattan Hurevich、Avi Swed、Salim Joubran、Shira Cohen、Noam S. Freeman、Elena Britan-Rosich、Laurence Briant-Longuet、Martine Bardy、Christian Devaux、Moshe Kotler、Amnon Hoffman、Chaim Gilon

  DOI：10.1016/j.bmc.2010.04.053

  日期：2010.8

  Rational conversion of noncontinuous active regions of proteins into a small orally bioavailable molecule is crucial for the discovery of new drugs based on inhibition of protein-protein interactions. We developed a method that utilizes backbone cyclization as an intermediate step for conversion of the CD4 noncontinuous active region into small macrocyclic molecules. We demonstrate that this method is feasible by preparing small inhibitor for human immunodeficiency virus infection. The lead compound, CG-1, proved orally available in the rat model. (C) 2010 Elsevier Ltd. All rights reserved.