Z-Thr-Pro-OMe | 76264-51-2

• 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-Thr-Pro-OMe
• 英文别名: methyl (2S)-1-[(2S,3R)-3-hydroxy-2-(phenylmethoxycarbonylamino)butanoyl]pyrrolidine-2-carboxylate
• CAS: 76264-51-2
• 化学式: C₁₈H₂₄N₂O₆
• 分子量: 364.398
• InChiKey: MNOROCMKYLCNJN-SNPRPXQTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  105
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Z-Thr-Pro-OMe 在 lithium hydroxide monohydrate 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 水 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 6.0h， 生成 methyl (2-((S)-1-(((benzyloxy)carbonyl)-L-threonyl)pyrrolidine-2-carboxamido)-2-methylpropanoyl)-L-alaninate
  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-苄氧羰基-L-苏氨酸 、 L-脯氨酸甲酯盐酸盐 在 碳酸氢钠 、 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 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以94%的产率得到Z-Thr-Pro-OMe
  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

文献信息

• Conformation-dependent O-glycosylation of threonine-containing dipeptides
  作者：N.Joe Maeji、Yoshio Inoue、Riichirô Chûjô

  DOI：10.1016/0008-6215(86)85036-4

  日期：1986.1