(2S,3R)-3-amino-2-hydroxy-4-p-aminophenylbutanoyl-(S)-leucine

• 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: (2S,3R)-3-amino-2-hydroxy-4-p-aminophenylbutanoyl-(S)-leucine
• 英文别名: (2S,3R)-3-Amino-2-hydroxy-4-p-aminophenylbutanoyl-(S)-leucin；(2S)-2-[[(2S,3R)-3-amino-4-(4-aminophenyl)-2-hydroxybutanoyl]amino]-4-methylpentanoic acid
• 化学式: C₁₆H₂₅N₃O₄
• 分子量: 323.392
• InChiKey: MRAKMZPMOSJIRW-RDBSUJKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  139
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  乌苯美司 在 钯 氢气 作用下， 以 甲醇 为溶剂， 生成 (2S,3R)-3-amino-2-hydroxy-4-p-aminophenylbutanoyl-(S)-leucine
  参考文献：
  名称：

  Synthesis and structure-activity relations of bestatin analogs, inhibitors of aminopeptidase B

  摘要：

  Stereoisomers and analogues of bestatin, [(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoyl]-L-leucine, were synthesized and tested for aminopeptidase B and leucine aminopeptidase inhibiting activity. Among the eight stereoisomers, the 2S stereoisomers exhibited strong activity. In a series of compounds in which the L-leucine residue of bestatin was substituted with other amino acids, only the one containing isoleucine showed more activity than bestatin. Norleucine, norvaline, methionine, valine, serine, glutamine, phenylalanine, glutamic acid, proline, and lysine analogues gave, in that order, decreasing activity. Alkyl and phenyl sub stitution for the benzyl group of bestatin decreased the activity markedly. p-Methyl-, p-chloro-, and p-nitrobestatins showed greater activity than bestatin.

  DOI：

  10.1021/jm00214a010

文献信息

• FR2318863
  申请人：——

  公开号：——

  公开（公告）日：——
• US4281180A
  申请人：——

  公开号：US4281180A

  公开（公告）日：1981-07-28
• US4391986A
  申请人：——

  公开号：US4391986A

  公开（公告）日：1983-07-05
• US4453003A
  申请人：——

  公开号：US4453003A

  公开（公告）日：1984-06-05
• Synthesis and structure-activity relations of bestatin analogs, inhibitors of aminopeptidase B
  作者：Rinzo Nishizawa、Tetsushi Saino、Tomohisa Takita、Hiroyuki Suda、Takaaki Aoyagi、Hamao Umezawa

  DOI：10.1021/jm00214a010

  日期：1977.4

  Stereoisomers and analogues of bestatin, [(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoyl]-L-leucine, were synthesized and tested for aminopeptidase B and leucine aminopeptidase inhibiting activity. Among the eight stereoisomers, the 2S stereoisomers exhibited strong activity. In a series of compounds in which the L-leucine residue of bestatin was substituted with other amino acids, only the one containing isoleucine showed more activity than bestatin. Norleucine, norvaline, methionine, valine, serine, glutamine, phenylalanine, glutamic acid, proline, and lysine analogues gave, in that order, decreasing activity. Alkyl and phenyl sub stitution for the benzyl group of bestatin decreased the activity markedly. p-Methyl-, p-chloro-, and p-nitrobestatins showed greater activity than bestatin.