Cbz-Leu-D-Leu-OMe | 71730-80-8

• 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: Cbz-Leu-D-Leu-OMe
• 英文别名: Z-L-Leu-D-Leu-OMe；N-(N-benzyloxycarbonyl-L-leucyl)-D-leucine methyl ester；N-(N-Benzyloxycarbonyl-L-leucyl)-D-leucin-methylester；Benzyloxycarbonyl-(S)-leucyl-(R)-leucin-methylester；methyl (2R)-4-methyl-2-[[(2S)-4-methyl-2-(phenylmethoxycarbonylamino)pentanoyl]amino]pentanoate
• CAS: 71730-80-8
• 化学式: C₂₁H₃₂N₂O₅
• 分子量: 392.495
• InChiKey: FYKHRTVYUNLJLJ-ZWKOTPCHSA-N

物化性质

• 熔点：
  81.5-82.5 °C
• 沸点：
  546.5±40.0 °C(Predicted)
• 密度：
  1.090±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  28
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  93.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Cbz-Leu-D-Leu-OMe 在 sodium hydroxide 、 palladium on activated charcoal 、 乙醇 作用下， 生成 L-亮氨酰-D-亮氨酸二水合物
  参考文献：
  名称：

  Smith et al., Journal of Biological Chemistry, 1952, vol. 199, p. 801,808

  摘要：

  DOI：
• 作为产物：
  描述：

  L-亮氨酸 在 sodium hydroxide 作用下， 生成 Cbz-Leu-D-Leu-OMe
  参考文献：
  名称：

  Herlinger,H. et al., Justus Liebigs Annalen der Chemie, 1967, vol. 706, p. 37 - 46

  摘要：

  DOI：

文献信息

• Facile Synthesis of Cyclic Dipeptides and Detection of Racemization
  作者：Toshihisa Ueda、Morinobu Saito、Tetsuo Kato、Nobuo Izumiya

  DOI：10.1246/bcsj.56.568

  日期：1983.2

  Several cyclic dipeptides were synthesized by refluxing methanolic solution of dipeptide methyl esters in high yield and purity. Cyclic dipeptides prepared by the Fischer method, the Nitecki method, and the present methanol-reflux method were compared with respect to yield and optical purity. The methanol-reflux method usually gave good results. High-performance liquid chromatography was effectively applied to detect racemization.

  通过回流二肽甲酯的甲醇溶液，合成了几个高产率和高纯度的环状二肽。通过Fischer法、Nitecki法和当前的甲醇回流法准备的环状二肽，在产率和光学纯度方面进行了比较。甲醇回流法通常能得到良好的结果。高效液相色谱法有效地应用于检测外消旋化。
• α-Chymotrypsin-catalyzed peptide synthesis in frozen aqueous solution using N-protected amino acid carbamoylmethyl esters as acyl donors
  作者：Sayed Mohiuddin Abdus Salam、Ken-ichi Kagawa、Katsuhiro Kawashiro

  DOI：10.1016/j.tetasy.2005.10.042

  日期：2006.1

  A kinetically controlled peptide synthesis catalyzed by alpha-chymotrypsin was performed in frozen aqueous solution (ice, -24 degrees C). The yield of the peptide was significantly improved by the use of the carbamoylmethyl (Cam) ester as the acyl donor instead of the conventional ethyl ester. The peptide yield increased up to ca. 90% when N-benzyloxycarbonyl (CBZ)-Phe-OCam and H-Phe-NH2 were used as the acyl donor and nucleophile, respectively. Such an improvement of the peptide yield in ice was also observed in the coupling of other CBZ-amino acid Cam esters as acyl donors. Furthermore, this approach was applied to the synthesis of peptides containing D-amino acids. The peptides such as CBZ-D-Phe-Phe-NH2, CBZ-Phe-D-Phe-NH2 and CBZ-D-Phe-D-Phe-NH2 were also obtained in excellent to moderate yields in ice. A high diastereoselectivity towards the L-L peptide was observed when the racemic amino acid Cam ester was used as the acyl donor in ice. (c) 2005 Elsevier Ltd. All rights reserved.
• Herlinger,H. et al., Justus Liebigs Annalen der Chemie, 1967, vol. 706, p. 37 - 46
  作者：Herlinger,H. et al.

  DOI：——

  日期：——
• Smith et al., Journal of Biological Chemistry, 1952, vol. 199, p. 801,808
  作者：Smith et al.

  DOI：——

  日期：——