(S)-2-tert-Butoxycarbonylamino-2-[(2S,5'S,5''S)-5',5''-diisobutyl-2-isopropyl-5''-(3-methyl-but-2-enyl)-3,4',4''-trioxo-2,3,4',5',4'',5''-hexahydro-1H,1'H,1''H-[2,3';5',3'']terpyrrol-4-yl]-3-phenyl-propionic acid methyl ester | 145452-06-8

• 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: (S)-2-tert-Butoxycarbonylamino-2-[(2S,5'S,5''S)-5',5''-diisobutyl-2-isopropyl-5''-(3-methyl-but-2-enyl)-3,4',4''-trioxo-2,3,4',5',4'',5''-hexahydro-1H,1'H,1''H-[2,3';5',3'']terpyrrol-4-yl]-3-phenyl-propionic acid methyl ester
• 英文别名: methyl (2S)-2-[(5S)-5-[(5S)-5-[(5S)-5-(3-methylbut-2-enyl)-5-(2-methylpropyl)-4-oxo-1H-pyrrol-3-yl]-5-(2-methylpropyl)-4-oxo-1H-pyrrol-3-yl]-4-oxo-5-propan-2-yl-1H-pyrrol-3-yl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoate
• CAS: 145452-06-8
• 化学式: C₄₃H₆₀N₄O₇
• 分子量: 744.972
• InChiKey: HQOOEAAQVUQQKH-NCZZEDDZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.9
• 重原子数：
  54
• 可旋转键数：
  17
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  152
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (S)-2-tert-Butoxycarbonylamino-2-[(2S,5'S,5''S)-5',5''-diisobutyl-2-isopropyl-5''-(3-methyl-but-2-enyl)-3,4',4''-trioxo-2,3,4',5',4'',5''-hexahydro-1H,1'H,1''H-[2,3';5',3'']terpyrrol-4-yl]-3-phenyl-propionic acid methyl ester 在 sodium periodate 、 四氧化锇 、 双(三甲基硅烷基)氨基钾 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 氯仿 、 水 、 丙酮 、 甲苯 、 苯 为溶剂， 反应 25.25h， 生成 methyl (2S)-2-[(5S)-5-[(5S)-5-[(5S)-5-[(5R)-5-benzyl-5-(3-methylbut-2-enyl)-4-oxo-1H-pyrrol-3-yl]-5-(2-methylpropyl)-4-oxo-1H-pyrrol-3-yl]-5-(2-methylpropyl)-4-oxo-1H-pyrrol-3-yl]-4-oxo-5-propan-2-yl-1H-pyrrol-3-yl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoate
  参考文献：
  名称：

  De Novo Design, Synthesis, and X-ray Crystal Structures of Pyrrolinone-Based .beta.-Strand Peptidomimetics

  摘要：

  The de novo design and synthesis of a novel non-peptide scaffolding for beta-strand/sheet mimics are described. The scaffold consists of repeating 3,5,5-trisubstituted pyrrolinone (enaminone) units punctuated with appropriate amino acid side chains. The iterative construction of the pyrrolinones exploits a highly efficient cyclization of metalloimines, the latter derived from C-terminal aldehydes and readily available alpha-substituted alpha-amino ester building blocks. As predicted by interactive computer modeling and confirmed by X-ray crystallography, the polypyrrolinones present the side chains and carbonyl hydrogen-bond accepters in a solid-state conformation which mimics polypeptide beta-sheets. Importantly, the enaminone NH protons form hydrogen bonds both intramolecularly, stabilizing the beta-strand conformation, and intermolecularly, promoting sheet formation. The presence or absence of the nitrogen protecting group controlled antiparallel versus parallel sheet formation.

  DOI：

  10.1021/ja00101a017
• 作为产物：
  描述：

  (R)-2-Amino-2-benzyl-5-methyl-hex-4-enoic acid methyl ester 在 sodium periodate 、 四氧化锇 、 双(三甲基硅烷基)氨基钾 、 臭氧 、 N-甲基吗啉氧化物 、 三苯基膦 作用下， 以 四氢呋喃 、 氯仿 、 水 、 丙酮 、 甲苯 为溶剂， 反应 67.09h， 生成 (S)-2-tert-Butoxycarbonylamino-2-[(2S,5'S,5''S)-5',5''-diisobutyl-2-isopropyl-5''-(3-methyl-but-2-enyl)-3,4',4''-trioxo-2,3,4',5',4'',5''-hexahydro-1H,1'H,1''H-[2,3';5',3'']terpyrrol-4-yl]-3-phenyl-propionic acid methyl ester
  参考文献：
  名称：

  De Novo Design, Synthesis, and X-ray Crystal Structures of Pyrrolinone-Based .beta.-Strand Peptidomimetics

  摘要：

  The de novo design and synthesis of a novel non-peptide scaffolding for beta-strand/sheet mimics are described. The scaffold consists of repeating 3,5,5-trisubstituted pyrrolinone (enaminone) units punctuated with appropriate amino acid side chains. The iterative construction of the pyrrolinones exploits a highly efficient cyclization of metalloimines, the latter derived from C-terminal aldehydes and readily available alpha-substituted alpha-amino ester building blocks. As predicted by interactive computer modeling and confirmed by X-ray crystallography, the polypyrrolinones present the side chains and carbonyl hydrogen-bond accepters in a solid-state conformation which mimics polypeptide beta-sheets. Importantly, the enaminone NH protons form hydrogen bonds both intramolecularly, stabilizing the beta-strand conformation, and intermolecularly, promoting sheet formation. The presence or absence of the nitrogen protecting group controlled antiparallel versus parallel sheet formation.

  DOI：

  10.1021/ja00101a017

文献信息

• Design, synthesis, and crystal structure of a pyrrolinone-based peptidomimetic possessing the conformation of a .beta.-strand: potential application to the design of novel inhibitors of proteolytic enzymes
  作者：Amos B. Smith、Terence P. Keenan、Ryan C. Holcomb、Paul A. Sprengeler、Mark C. Guzman、John L. Wood、Patrick J. Carroll、Ralph Hirschmann

  DOI：10.1021/ja00052a093

  日期：1992.12