N-Boc-L-(ω-nitro)arginyl-L-valine benzyl ester | 51165-68-5

• 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: N-Boc-L-(ω-nitro)arginyl-L-valine benzyl ester
• 英文别名: Boc-Arg(NO2)-Val-OBn；benzyl (2S)-2-[[(2S)-5-[[amino(nitramido)methylidene]amino]-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoyl]amino]-3-methylbutanoate
• CAS: 51165-68-5
• 化学式: C₂₃H₃₆N₆O₇
• 分子量: 508.575
• InChiKey: VHRJDEACGGLKIK-ROUUACIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  36
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  190
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N-Boc-L-(ω-nitro)arginyl-L-valine benzyl ester 在 盐酸 、 四丁基氟化铵 、 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 4.5h， 生成 N-{N-[(2S)-4-oxoazetidine-2-carbonyl]-L-(ω-nitro)arginyl}-L-valine benzyl ester
  参考文献：
  名称：

  β-Lactam Derivatives as Enzyme Inhibitors: Carboxy Peptidyl Derivatives of (S)-4-Oxoazetidine-2-carboxylate as Peptidomimetics

  摘要：

  4-Oxoazetidine-2-carboxylic acid, protected at the nitrogen by silyl groups, was coupled with amino acid and oligopeptide esters. Desilylation and deprotection of the amino acid residues yielded the free beta -lactam peptides. Structure and properties were elucidated by spectroscopic methods and discussed. Some selected compounds were tested as fibrinogen inhibitors and for thrombocyte aggregation. None of the compounds showed any activity up to a concentration of 10(-5) Mol/l. Some other compounds exhibited a weak inhibitory activity against elastase (PPE).

  DOI：

  10.1002/1521-4184(200105)334:5<167::aid-ardp167>3.3.co;2-f
• 作为产物：
  描述：

  N-Boc-N'-硝基-L-精氨酸 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.25h， 生成 N-Boc-L-(ω-nitro)arginyl-L-valine benzyl ester
  参考文献：
  名称：

  氨基酸和多肽。十七。与血纤蛋白α-链的N端部分有关的肽的合成及其对血纤蛋白原/凝血酶凝血的抑制作用。

  摘要：

  通过溶液法和固相法合成了与纤维蛋白α链的N末端部分有关的各种肽，并研究了它们对纤维蛋白原/凝血酶凝血的抑制作用。N端三肽的肽链延伸降低了抑制作用。N端十肽类似物H-Gly-Pro-Arg-Pro-Pro-Glu-Arg-His-Gln-Ser-NH2显示了最有效的作用。

  DOI：

  10.1248/cpb.41.525

文献信息

• Amino Acids and Peptides. XVII. Synthesis of Peptides Related to N-Terminal Portion of Fibrin .ALPHA.-Chain and Their Inhibitory Effect on Fibrinogen/Thrombin Clotting.
  作者：Koichi KAWASAKI、Toshiki TSUJI、Katuhiko HIRASE、Masanori MIYANO、Sachiye INOUE、Masahiro IWAMOTO

  DOI：10.1248/cpb.41.525

  日期：——

  Various peptides related to N-terminal portion of fibrin alpha-chain were synthesized by the solution method and the solid-phase method, and their inhibitory effect on fibrinogen/thrombin clotting was examined. Extension of peptide chain from N-terminal tripeptide decreased the inhibitory effect. The most potent effect was shown by N-terminal decapeptide analog, H-Gly-Pro-Arg-Pro-Pro-Glu-Arg-His-Gln-Ser-NH2

  通过溶液法和固相法合成了与纤维蛋白α链的N末端部分有关的各种肽，并研究了它们对纤维蛋白原/凝血酶凝血的抑制作用。N端三肽的肽链延伸降低了抑制作用。N端十肽类似物H-Gly-Pro-Arg-Pro-Pro-Glu-Arg-His-Gln-Ser-NH2显示了最有效的作用。
• β-Lactam Derivatives as Enzyme Inhibitors: Carboxy Peptidyl Derivatives of (S)-4-Oxoazetidine-2-carboxylate as Peptidomimetics
  作者：Martin Schneider、Hans-Hartwig Otto

  DOI：10.1002/1521-4184(200105)334:5<167::aid-ardp167>3.3.co;2-f

  日期：2001.5

  4-Oxoazetidine-2-carboxylic acid, protected at the nitrogen by silyl groups, was coupled with amino acid and oligopeptide esters. Desilylation and deprotection of the amino acid residues yielded the free beta -lactam peptides. Structure and properties were elucidated by spectroscopic methods and discussed. Some selected compounds were tested as fibrinogen inhibitors and for thrombocyte aggregation. None of the compounds showed any activity up to a concentration of 10(-5) Mol/l. Some other compounds exhibited a weak inhibitory activity against elastase (PPE).