glycyl-L-leucine benzyl ester hydrochloride

• 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: glycyl-L-leucine benzyl ester hydrochloride
• 英文别名: benzyl (2S)-2-[(2-aminoacetyl)amino]-4-methylpentanoate;hydrochloride
• 化学式: C₁₅H₂₂N₂O₃*ClH
• 分子量: 314.812
• InChiKey: OTQRYPLNVOKJTE-ZOWNYOTGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.64
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  81.4
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  glycyl-L-leucine benzyl ester hydrochloride 、 甘草酸 在 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 、 三乙胺 作用下， 以 1,4-二氧六环 为溶剂， 生成
  参考文献：
  名称：

  Synthesis and biological activity of new glycyrrhizic acid conjugates with amino acids and dipeptides

  摘要：

  New glycyrrhizic acid (GA) conjugates were synthesized with the use of tert-butyl esters of amino acids or benzyl esters of dipeptides; they contained two residues of L-amino acids (Met, Phe, Pro, and Ile or dipeptides Gly-Leu and Gly-Phe). Activation of GA carboxy groups was carried out with the help of N-hydroxysuccinimide, N,N'-dicyclohexylcarbodiimide, or N-hydroxybenzotriazole with dicyclohexylcarbodiimide. A proline-containing GA derivative is a low-toxic substance; it raises the level of agglutinins by 3.7 times in the blood of mice and 3 times that of hemolysins compared with the control. Dipeptide GA derivatives possess an expressed anti-HIV-1 activity in cultures of MT-4 cells and are 90-70 times less cytotoxic than azidothymidine. The selectivity index of the compounds exceeds those of GA by 110 and 34 times, respectively.

  DOI：

  10.1134/s1068162009040141
• 作为产物：
  描述：

  L-亮氨酸苄酯对甲苯磺酸盐 在 盐酸 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 24.17h， 生成 glycyl-L-leucine benzyl ester hydrochloride
  参考文献：
  名称：

  通过Pd / Cu双催化对氨基酸和小肽进行立体选择性和特定位烯丙基烷基化

  摘要：

  我们报告的席夫碱活化的氨基酸和小肽通过Pd / Cu双重催化的立体选择性和特定位置的烯丙基烷基化。容易地以高收率和优异的对映选择性（高达> 99％ee）合成一系列非编码的α，α-二烷基α-氨基酸。此外，使用该双重催化剂体系完成了在特定位点掺入对映体纯的α-烷基或α，α-二烷基α-氨基酸残基的小肽的直接和高度立体选择性的合成。

  DOI：

  10.1021/jacs.7b05460

文献信息

• US4092304A
  申请人：——

  公开号：US4092304A

  公开（公告）日：1978-05-30
• Stereoselective and Site-Specific Allylic Alkylation of Amino Acids and Small Peptides via a Pd/Cu Dual Catalysis
  作者：Xiaohong Huo、Rui He、Jingke Fu、Jiacheng Zhang、Guoqiang Yang、Wanbin Zhang

  DOI：10.1021/jacs.7b05460

  日期：2017.7.26

  alkylation of Schiff base activated amino acids and small peptides via a Pd/Cu dual catalysis. A range of noncoded α,α-dialkyl α-amino acids were easily synthesized in high yields and with excellent enantioselectivities (up to >99% ee). Furthermore, a direct and highly stereoselective synthesis of small peptides with enantiopure α-alkyl or α,α-dialkyl α-amino acids residues incorporated at specific sites

  我们报告的席夫碱活化的氨基酸和小肽通过Pd / Cu双重催化的立体选择性和特定位置的烯丙基烷基化。容易地以高收率和优异的对映选择性（高达> 99％ee）合成一系列非编码的α，α-二烷基α-氨基酸。此外，使用该双重催化剂体系完成了在特定位点掺入对映体纯的α-烷基或α，α-二烷基α-氨基酸残基的小肽的直接和高度立体选择性的合成。
• Synthesis and biological activity of new glycyrrhizic acid conjugates with amino acids and dipeptides
  作者：L. A. Baltina、R. M. Kondratenko、L. A. Baltina、N. Z. Baschenko、O. A. Pl’yasunova

  DOI：10.1134/s1068162009040141

  日期：2009.7

  New glycyrrhizic acid (GA) conjugates were synthesized with the use of tert-butyl esters of amino acids or benzyl esters of dipeptides; they contained two residues of L-amino acids (Met, Phe, Pro, and Ile or dipeptides Gly-Leu and Gly-Phe). Activation of GA carboxy groups was carried out with the help of N-hydroxysuccinimide, N,N'-dicyclohexylcarbodiimide, or N-hydroxybenzotriazole with dicyclohexylcarbodiimide. A proline-containing GA derivative is a low-toxic substance; it raises the level of agglutinins by 3.7 times in the blood of mice and 3 times that of hemolysins compared with the control. Dipeptide GA derivatives possess an expressed anti-HIV-1 activity in cultures of MT-4 cells and are 90-70 times less cytotoxic than azidothymidine. The selectivity index of the compounds exceeds those of GA by 110 and 34 times, respectively.