L-leucine N-phenethylamide | 87176-71-4

• 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: L-leucine N-phenethylamide
• 英文别名: (2S)-2-amino-4-methyl-N-(2-phenylethyl)pentanamide
• CAS: 87176-71-4
• 化学式: C₁₄H₂₂N₂O
• mdl: MFCD09724993
• 分子量: 234.341
• InChiKey: XTVMZZSWRGAPKM-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  55.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  L-leucine N-phenethylamide 在 palladium on activated charcoal N-羟基丁二酰亚胺 、 氢气 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 为溶剂， 25.0 ℃ 、2.0 MPa 条件下， 反应 13.67h， 生成 L-alanyl-L-alanyl-L-leucine 2-phenylethylamide
  参考文献：
  名称：

  Kasafirek, Evzen; Sutiakova, Irena; Bartik, Michal, Collection of Czechoslovak Chemical Communications, 1988, vol. 53, # 11B, p. 2877 - 2883

  摘要：

  DOI：
• 作为产物：
  描述：

  benzyloxycarbonylleucine 2-phenylethylamide 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 0.33h， 生成 L-leucine N-phenethylamide
  参考文献：
  名称：

  Kasafirek, Evzen; Sutiakova, Irena; Bartik, Michal, Collection of Czechoslovak Chemical Communications, 1988, vol. 53, # 11B, p. 2877 - 2883

  摘要：

  DOI：

文献信息

• Carboxyalkyl peptide derivatives
  申请人：G.D. Searle & Co.

  公开号：US04511504A1

  公开（公告）日：1985-04-16

  This invention encompasses novel carboxyalkyl peptide derivatives which are collagenase inhibitors.

  这项发明涵盖了新型的羧基烷基肽衍生物，它们是胶原酶抑制剂。
• Carboxylalkyl peptide derivatives
  申请人：G. D. Searle & Co.

  公开号：US04568666A1

  公开（公告）日：1986-02-04

  This invention encompasses novel carboxyalkyl peptide derivatives which are collagenase inhibitors.

  这项发明涵盖了一种新型的羧基烷基肽衍生物，它们是胶原酶抑制剂。
• PEPTIDE DERIVATIVES AND ANGIOTENSIN IV RECEPTOR AGONIST
  申请人：SAGAMI CHEMICAL RESEARCH CENTER

  公开号：EP0838471A1

  公开（公告）日：1998-04-29

  Short-chain peptide derivatives acting on angiotensin IV receptor at low concentrations. Because of agonistically acting on angiotensin IV receptor, the novel peptide derivatives of the present invention represented by the following formula (1) are useful as remedies for various diseases in which angiotensin IV participates:

  低浓度作用于血管紧张素 IV 受体的短链肽衍生物。由于对血管紧张素 IV 受体具有激动作用，下式（1）所代表的本发明新型肽衍生物可用于治疗血管紧张素 IV 参与作用的各种疾病：
• Malonyl α-mercaptoketones and α-mercaptoalcohols, a new class of matrix metalloproteinase inhibitors
  作者：David A. Campbell、Xiao-Yi Xiao、David Harris、Satoru Ida、Reza Mortezaei、Khehyong Ngu、Lihong Shi、David Tien、Yongwen Wang、Marc Navre、Dinesh V. Patel、Michele A. Sharr、John F. DiJoseph、Loran M. Killar、Christina L. Leone、Jeremy I. Levin、Jerauld S. Skotnicki

  DOI：10.1016/s0960-894x(98)00185-1

  日期：1998.5

  A novel series of matrix metalloproteinase (MMP) inhibitors is described. Incorporation of a terminal alpha-mercaptoketone or alpha-mercaptoalcohol in the zinc binding domain of a series of inhibitors led to compounds exhibiting low nanomolar activity against collagenase-1 (MMP-1), stromelysin (MMP-3), and gelatinase-B (MMP-9). (C) 1998 Elsevier Science Ltd. All rights reserved.
• The urea-dipeptides show stronger H-bonding propensity to nucleate β-sheetlike assembly than natural sequence
  作者：Damei Ke、Chuanlang Zhan、Xiao Li、Alexander D.Q. Li、Jiannian Yao

  DOI：10.1016/j.tet.2009.07.048

  日期：2009.9

  In this article, we report the distinct solution behavior of a set of urea-dipeptides to that of natural sequence. The urea-dipeptides adopt beta-folding conformations and form into beta-sheetlike assembly in chloroform. Most surprisedly, the urea-dipeptides tend to form interpeptide H-bonding interactions even at a concentration of as low as 0 1 mM, while the natural sequence shows H-bonding propensity at a concentration of about 7 mM, indicating that the urea-dipeptides Show Much stronger H-bonding propensity to nucleate formation of beta-sheetlike assembly than the natural sequence CD spectra reveal that the investigated urea-dipeptides have two negative CD bands, respectively, around 217 nm and 224 nm, supporting the beta-folding conformations and in turn formation of beta-sheetlike assembly. The beta-sheetlike assembly is also confirmed by the XRD reflections, which give two typical d-spacings of 12 7 and 4 8 angstrom, respectively, corresponding to stacking periodicity of the beta-sheets and the spacing between peptide backbones running orthogonal to the beta-sheet axis. (C) 2009 Elsevier Ltd All rights reserved