Z-ΔAla-L-Pro-OMe | 126749-83-5

• 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-ΔAla-L-Pro-OMe
• 英文别名: methyl (2-(((benzyloxy)carbonyl)amino)acryloyl)-L-prolinate
• CAS: 126749-83-5
• 化学式: C₁₇H₂₀N₂O₅
• 分子量: 332.356
• InChiKey: FSUDJKXVVQCTFM-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.59
• 重原子数：
  24.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  84.94
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  Z-ΔAla-L-Pro-OMe 在 lithium hydroxide monohydrate 作用下， 以 水 、 叔丁醇 为溶剂， 反应 4.0h， 以73%的产率得到
  参考文献：
  名称：

  Impact of Dehydroamino Acids on the Structure and Stability of Incipient 3₁₀-Helical Peptides

  摘要：

  A comparative study of the impact of small, medium-sized, and bulky alpha,beta-dehydroamino acids (Delta AAs) on the structure and stability of Balarams incipient 3(10)-helical peptide (1) is reported. Replacement of the N-terminal Aib residue of 1 with a Delta AA afforded peptides 2a-c that maintained the 3(10)-helical shape of 1. In contrast, installation of a Delta AA in place of Aib-3 yielded peptides 3a-c that preferred a beta-sheet-like conformation. The impact of the Delta AA on peptide structure was independent of size, with small (Delta Ala), medium-sized (Z-Delta Abu), and bulky (Delta Val) Delta AAs exerting similar effects. The proteolytic stabilities of 1 and its analogs were determined by incubation with Pronase. Z-Delta Abu and Delta Val increased the resistance of peptides to proteolysis when incorporated at the 3-position and had negligible impact on stability when placed at the 1-position, whereas Delta Ala-containing peptides degraded rapidly regardless of position. Exposure of peptides 2a-c and 3a-c to the reactive thiol cysteamine revealed that Delta Ala-containing peptides underwent conjugate addition at room temperature, while Z-Delta Abu- and Delta Val-containing peptides were inert even at elevated temperatures. These results suggest that both bulky and more accessible medium-sized Delta AAs should be valuable tools for bestowing rigidity and proteolytic stability on bioactive peptides.

  DOI：

  10.1021/acs.joc.9b02747
• 作为产物：
  描述：

  N-benzyloxycarbonyl-L-β-chloroalanine pentafluorophenyl ester 在 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 2.0h， 生成 Z-ΔAla-L-Pro-OMe
  参考文献：
  名称：

  自由基加至含有脱氢丙氨酸残基的二肽和三肽中

  摘要：

  通过烷基汞卤化物/硼氢化钠方法向含有脱氢丙氨酸残基的二肽和三肽中进行自由基加成反应，收率平稳，化学收率良好，但对映体对二肽和三肽的非对映选择性低。

  DOI：

  10.1016/s0040-4020(01)89507-7