Z-Ile-Leu | 38972-95-1

• 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: Z-Ile-Leu
• 英文别名: N-[(Benzyloxy)carbonyl]-L-Isoleucyl-L-Leucine；(2S)-4-methyl-2-[[(2S,3S)-3-methyl-2-(phenylmethoxycarbonylamino)pentanoyl]amino]pentanoic acid
• CAS: 38972-95-1
• 化学式: C₂₀H₃₀N₂O₅
• 分子量: 378.469
• InChiKey: BSRAGXJNZJMFMY-XIRDDKMYSA-N

物化性质

• 熔点：
  130-131℃
• 沸点：
  598.0±45.0 °C(Predicted)
• 密度：
  1.130±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  27
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Z-Ile-Leu 在 钯 氢气 、 溶剂黄146 作用下， 以 甲醇 、 水 为溶剂， 生成 L-异亮酰胺-L-亮氨酸
  参考文献：
  名称：

  槲寄生的化学研究。二、Viscumamide 的结构，一种从 Viscum albumLinn.var.coloratum Ohwi 中分离的新环状肽

  摘要：

  从 Viscum album Linn 中分离出一种新的环肽，viscumamide (C30H55N5O5)。变种 coloratum Ohwi，根据对部分水解产物的气相色谱研究，该物质的结构为 Ia（备注：省略图形。）。

  DOI：

  10.1246/bcsj.46.2190
• 作为产物：
  描述：

  N-苄氧羰基-L-异亮氨酸 在 sodium hydroxide 作用下， 以 丙酮 为溶剂， 生成 Z-Ile-Leu
  参考文献：
  名称：

  槲寄生的化学研究。二、Viscumamide 的结构，一种从 Viscum albumLinn.var.coloratum Ohwi 中分离的新环状肽

  摘要：

  从 Viscum album Linn 中分离出一种新的环肽，viscumamide (C30H55N5O5)。变种 coloratum Ohwi，根据对部分水解产物的气相色谱研究，该物质的结构为 Ia（备注：省略图形。）。

  DOI：

  10.1246/bcsj.46.2190

文献信息

• Evolution, synthesis and SAR of tripeptide α-ketoacid Inhibitors of the hepatitis C virus NS3/NS4A serine protease
  作者：Stefania Colarusso、Benjamin Gerlach、Uwe Koch、Ester Muraglia、Immacolata Conte、Ian Stansfield、Victor G Matassa、Frank Narjes

  DOI：10.1016/s0960-894x(01)00843-5

  日期：2002.2

  N-terminal truncation of the hexapeptide ketoacid 1 gave rise to potent tripeptide inhibitors of the hepatitis C virus NS3 protease/NS4A cofactor complex. Optimization of these tripeptides led to ketoacid 30 with an IC50 of 0.38 microM. The SAR of these tripeptides is discussed in the light of the recently published crystal structures of a ternary tripetide/NS3/NS4A complexes.

  六肽酮酸1的N端截短产生了丙型肝炎病毒NS3蛋白酶/ NS4A辅因子复合物的有效三肽抑制剂。这些三肽的优化产生了酮酸30，IC50为0.38 microM。鉴于最近公布的三元三元/ / NS4A配合物的晶体结构，讨论了这些三元的SAR。
• Facile synthesis of amino acid and peptide esters under mild conditions via cesium salts
  作者：Su-Sun Wang、B. F. Gisin、D. P. Winter、R. Makofske、I. D. Kulesha、C. Tzougraki、J. Meienhofer

  DOI：10.1021/jo00428a004

  日期：1977.4
• Buchholz, Michael; Kunz, Horst, Liebigs Annalen der Chemie, 1983, # 11, p. 1859 - 1885
  作者：Buchholz, Michael、Kunz, Horst

  DOI：——

  日期：——
• Optimization of Subsite Binding to the β5 Subunit of the Human 20S Proteasome Using Vinyl Sulfones and 2-Keto-1,3,4-oxadiazoles:  Syntheses and Cellular Properties of Potent, Selective Proteasome Inhibitors
  作者：Robert M. Rydzewski、Leland Burrill、Rohan Mendonca、James T. Palmer、Mark Rice、Ram Tahilramani、Kathryn E. Bass、Ling Leung、Erik Gjerstad、James W. Janc、Lin Pan

  DOI：10.1021/jm058289o

  日期：2006.5.1

  Beginning with the peptide sequence Cbz-Ile-Glu(OtBu)-Ala-Leu found in PSI (3), a series of vinyl sulfones (VS) were synthesized for evaluation as inhibitors of the chymotrypsin-like activity of the 20S proteasome. Variations at the key P3 position confirmed the importance of a long side chain capped with a hydrophobic group for optimal potency, consistent with a model of binding to the S3 subsite. The tert-butyl glutamic ester initially used at P3 gave plasma unstable, insoluble compounds and was replaced with the better isostere, N-beta-neopentyl asparagine. The inhibitors were shortened by replacing the N-terminal Cbz-isoleucine with a p-tosyl group without loss of potency. Small L-amino acids were used at P2, where D-substitution was not tolerated. The resulting optimized P4-P3-P2 sequence was grafted onto a novel proteasome inhibitor warhead, 2-keto-1,3,4-oxadiazoles (KOD), to produce reversible, subnanomolar proteasome inhibitors that were 1000-fold selective versus cathepsin B (CatB), cathepsin S (CatS), and trypsin-like as well as PGPH-like proteasome activity. A number of compounds in both the VS and the KOD series exhibited growth inhibitory effects against the human prostate cancer cell line PC3 at submicromolar concentrations.
• THE SYNTHESIS OF SEVERAL ISOLEUCYL PEPTIDES AND CERTAIN OF THEIR PROPERTIES
  作者：D. THEODOROPOULOS、L. C. CRAIG

  DOI：10.1021/jo01126a004

  日期：1955.9