Boc-thionoAla-Ala-Phe-OMe | 206123-98-0

• 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: Boc-thionoAla-Ala-Phe-OMe
• 英文别名: methyl (2S)-2-[[(2S)-2-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanethioyl]amino]propanoyl]amino]-3-phenylpropanoate
• CAS: 206123-98-0
• 化学式: C₂₁H₃₁N₃O₅S
• 分子量: 437.56
• InChiKey: DXQDOFIJHGBZKS-DZKIICNBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  138
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  甲酰肼 、 Boc-thionoAla-Ala-Phe-OMe 在 mercury(II) diacetate 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以67%的产率得到(S)-2-{(S)-2-[3-((S)-1-tert-Butoxycarbonylamino-ethyl)-[1,2,4]triazol-4-yl]-propionylamino}-3-phenyl-propionic acid methyl ester
  参考文献：
  名称：

  A cis Amide Bond Surrogate Incorporating 1,2,4-Triazole

  摘要：

  A novel cis amide bond surrogate incorporating 1,2,4-triazole was designed and synthesized by the reaction of a thionotripeptide, formic hydrazide, and mercury(II) acetate. This method of surrogate formation was also applicable to a cyclic thionopeptide.

  DOI：

  10.1021/jo010904i
• 作为产物：
  描述：

  N-tert-butyloxycarbonylalanylphenylalanine methyl ester 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 生成 Boc-thionoAla-Ala-Phe-OMe
  参考文献：
  名称：

  Endothiopeptide inhibitors of HIV-1 protease

  摘要：

  Endothiopeptide inhibitors of HIV-1 protease were synthesized by chemical and enzymatic methods to individually replace each backbone amide bond in 1 with a thioamide-linkage. Interestingly, agent 7, which contains a thioamide-linkage between the P-2' and P-3' positions of 1, was the most potent, competitive inhibitor of HIV-1 protease with a K-i of 3.4 mu M. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00100-0

文献信息

• A <i>cis</i> Amide Bond Surrogate Incorporating 1,2,4-Triazole
  作者：Yukio Hitotsuyanagi、Shuichi Motegi、Haruhiko Fukaya、Koichi Takeya

  DOI：10.1021/jo010904i

  日期：2002.5.1

  A novel cis amide bond surrogate incorporating 1,2,4-triazole was designed and synthesized by the reaction of a thionotripeptide, formic hydrazide, and mercury(II) acetate. This method of surrogate formation was also applicable to a cyclic thionopeptide.
• Endothiopeptide inhibitors of HIV-1 protease
  作者：Shao Yao、Reena Zutshi、Jean Chmielewski

  DOI：10.1016/s0960-894x(98)00100-0

  日期：1998.3

  Endothiopeptide inhibitors of HIV-1 protease were synthesized by chemical and enzymatic methods to individually replace each backbone amide bond in 1 with a thioamide-linkage. Interestingly, agent 7, which contains a thioamide-linkage between the P-2' and P-3' positions of 1, was the most potent, competitive inhibitor of HIV-1 protease with a K-i of 3.4 mu M. (C) 1998 Elsevier Science Ltd. All rights reserved.