2-benzylamino-4-methylpentanoic acid (benzylcarbamoylmethyl)amide

• 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: 2-benzylamino-4-methylpentanoic acid (benzylcarbamoylmethyl)amide
• 英文别名: N-(N-benzyl-leucyl)-glycine benzylamide；N-(N-Benzyl-leucyl)-glycin-benzylamid；2-(benzylamino)-N-[2-(benzylamino)-2-oxoethyl]-4-methylpentanamide
• 化学式: C₂₂H₂₉N₃O₂
• 分子量: 367.491
• InChiKey: PHIIPFSLADABQM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  70.2
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-benzylamino-4-methylpentanoic acid (benzylcarbamoylmethyl)amide 、 苯甲酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Model Studies on the First Enzyme-Catalyzed Ugi Reaction

  摘要：

  Multicomponent reactions are powerful tools for organic chemistry, and among them, the Ugi reaction provides remarkable improvement in many fields of organic chemistry such us combinatorial chemistry, medicinal chemistry, and peptide chemistry. A new, enzyme-catalyzed example of the Ugi three-component reaction Is presented. The studies include the selection of an enzyme as well as determination of the scope and limitations of the newly described reaction. The presented method combines the enzyme promiscuity and multicomponent reaction advantages in the first one-pot formation of dipeptide 1.

  DOI：

  10.1021/ol3033829
• 作为产物：
  描述：

  (+/-)-N-(2-bromo-4-methyl-valeryl)-glycine 在 盐酸 、 甲醇 作用下， 生成 2-benzylamino-4-methylpentanoic acid (benzylcarbamoylmethyl)amide
  参考文献：
  名称：

  Abderhalden, Fermentforschung, 1938, vol. 15, p. 157,162,163

  摘要：

  DOI：

文献信息

• The influence of the isocyanoesters structure on the course of enzymatic Ugi reactions
  作者：Monika Wilk、Anna Brodzka、Dominik Koszelewski、Arleta Madej、Daniel Paprocki、Anna Żądło-Dobrowolska、Ryszard Ostaszewski

  DOI：10.1016/j.bioorg.2019.02.042

  日期：2019.12

  The impact of isocyanoesters structure on enzymatic three-component Ugi reactions course has been determined. The significant promiscuous ability of enzyme in Ugi-type reaction switching between four (U-4CR) and three (U-3CR) components reactions depending on the size of used isocyanoester. The application of short-chain cyanoesters up to isocyanpropionate leading to product of three component reaction

  已经确定了异氰酸酯结构对酶促三组分Ugi反应过程的影响。在Ugi型反应中，酶在4个（U-4CR）和3个（U-3CR）组分反应之间切换的显着混杂能力取决于所用异氰酸酯的大小。短链氰基酸酯的应用直至异氰酸丙酸酯仅导致三组分反应的产物，而较长的异氰基丁酸酯仅给出四组分反应的产物。研究的酶促Ugi反应的局限性是脂肪酶的底物选择性。
• Model Studies on the First Enzyme-Catalyzed Ugi Reaction
  作者：Szymon Kłossowski、Barbara Wiraszka、Stanisław Berłożecki、Ryszard Ostaszewski

  DOI：10.1021/ol3033829

  日期：2013.2.1

  Multicomponent reactions are powerful tools for organic chemistry, and among them, the Ugi reaction provides remarkable improvement in many fields of organic chemistry such us combinatorial chemistry, medicinal chemistry, and peptide chemistry. A new, enzyme-catalyzed example of the Ugi three-component reaction Is presented. The studies include the selection of an enzyme as well as determination of the scope and limitations of the newly described reaction. The presented method combines the enzyme promiscuity and multicomponent reaction advantages in the first one-pot formation of dipeptide 1.
• Abderhalden, Fermentforschung, 1938, vol. 15, p. 157,162,163
  作者：Abderhalden

  DOI：——

  日期：——