L-prolyl-L-proline | 20488-28-2

• 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: L-prolyl-L-proline
• 英文别名: Pro-Pro；H-Pro-Pro-OH；proline-proline；L-Proline dipeptide；(2S)-1-[(2S)-pyrrolidin-1-ium-2-carbonyl]pyrrolidine-2-carboxylate
• CAS: 20488-28-2
• 化学式: C₁₀H₁₆N₂O₃
• 分子量: 212.249
• InChiKey: RWCOTTLHDJWHRS-YUMQZZPRSA-N

物化性质

• 沸点：
  449.9±45.0 °C(Predicted)
• 密度：
  1.293±0.06 g/cm3(Predicted)
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  -2.3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  69.6
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  L-prolyl-L-proline 在 palladium on activated charcoal 氢气 、 三乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 31.0h， 生成 L-threonyl-L-lysyl-L-prolyl-L-proline
  参考文献：
  名称：

  Konopinska, Danuta, Polish Journal of Chemistry, 1982, vol. 56, # 4-6, p. 749 - 752

  摘要：

  DOI：
• 作为产物：
  描述：

  L-prolyl-L-proline hydrochloride 在 乙醇 、 sodium 作用下， 反应 2.0h， 以71%的产率得到L-prolyl-L-proline
  参考文献：
  名称：

  Synthesis of Prolylproline

  摘要：

  Prolylproline has been synthesized by both classical peptide synthesis method utilizing tert-butoxycarbonyl or trifluoroacetyl protection of the NH group and carbodiimide-promoted peptide bond formation and by opening of the dioxopiperazine ring in octahydrodipyrrolo[1,2-a:1 ',2 '-d]pyrazine-5,10-dione obtained by thermolysis of proline methyl ester.

  DOI：

  10.1134/s1070428019070169

文献信息

• The Enzyme‐Free Release of Nucleotides from Phosphoramidates Depends Strongly on the Amino Acid
  作者：Dejana Jovanovic、Peter Tremmel、Pradeep S. Pallan、Martin Egli、Clemens Richert

  DOI：10.1002/anie.202008665

  日期：2020.11.2

  Phosphoramidates composed of an amino acid and a nucleotide analogue are critical metabolites of prodrugs, such as remdesivir. Hydrolysis of the phosphoramidate liberates the nucleotide, which can then be phosphorylated to become the pharmacologically active triphosphate. Enzymatic hydrolysis has been demonstrated, but a spontaneous chemical process may also occur. We measured the rate of enzyme‐free

  由氨基酸和核苷酸类似物组成的氨基磷酸酯是瑞德西韦等前药的关键代谢物。氨基磷酸酯的水解释放出核苷酸，然后该核苷酸可以被磷酸化成具有药理活性的三磷酸盐。酶促水解已被证实，但也可能发生自发的化学过程。我们测量了 17 种核糖核苷酸的氨基磷酸酯与氨基酸或相关化合物在 pH 7.5 下的无酶水解速率。脯氨酸氨基磷酸酯快速水解，37°C 下含乙基咪唑的缓冲液中 Pro-AMP 的半衰期短至 2.4 小时；比 Ala-AMP 快 45 倍，比 Phe-AMP 快 120 倍。作为结晶伴侣与 RNase A 结合的 Gly-AMP、Pro-AMP、βPro-AMP 和 Phe-AMP 的晶体结构显示了羧酸盐如何很好地攻击氨基磷酸酯，从而有助于解释这种反应性。我们的结果对于新型抗病毒前药的设计具有重要意义。
• Studies of Bitter Peptides from Casein Hydrolyzate. VII. Bitterness of the retro-BPIa (Val–Ile–Phe–Pro–Pro–Gly–Arg) and Its Fragments
  作者：Toshiaki Shigenaga、Ken Otagiri、Hidenori Kanehisa、Hideo Okai

  DOI：10.1246/bcsj.57.103

  日期：1984.1

  To explain the bitter taste exhibited by BPIa (Arg–Gly–Pro–Pro–Phe–Ile–Val) which was isolated from casein hydrolyzate, we have proposed the following requirement: its characteristic spatial structure: the basic moiety in the N-terminal and the hydrophobic moiety in the C-terminal were affected to each other by prolylprolyl residue, is necessary for the bitterness to be exhibited. As for BPIc (Val–Tyr–Pro–Phe–Pro–Pro–Gly–Ile–Asn-His), which is the other fraction, although it exhibited as strong and bitter a taste as BPIa, the basic moiety of BPIc is located in the C-terminal and its hydrophobic moiety is located in the N-terminal. The authors synthesized retro-BPIa with the reverse peptide sequence and its fragments. The retro-BPIa exhibited as strong and bitter a taste as BPIa. However, the bitterness of the fragments of retro-BPIa was far weaker than that of retro-BPIa.

  为了说明从酪蛋白水解物中分离出的BPIa（Arg–Gly–Pro–Pro–Phe–Ile–Val）所表现出的苦味，我们提出了以下要求：其特征空间结构，即N末端的基本部分与C末端的疏水部分通过脯氨酸残基相互影响，是表现苦味所必需的。至于另一种成分BPIc（Val–Tyr–Pro–Phe–Pro–Pro–Gly–Ile–Asn-His），虽然它表现出的味道与BPIa一样强烈而苦涩，但BPIc的基本部分位于C末端，疏水部分位于N末端。作者合成了逆BPIa，其肽序列相反及其片段。逆BPIa表现出的苦味同样强烈，但逆BPIa片段的苦味远弱于逆BPIa。
• Dioxolane analogs for improved inter-cellular delivery
  申请人：Shire BioChem Inc.

  公开号：US20030013660A1

  公开（公告）日：2003-01-16

  Dioxolane analogs of the following formula: 1 wherein R1 and R2 are defined herein, are useful in the treatment of cancer. For example, the compounds can be used to treat patients with cancer in which the cancer cells are deficient in nucleoside or nucleoside base transporters.

  以下式中的二氧杂环戊烷类似物：其中R1和R2在此处定义，可用于治疗癌症。例如，这些化合物可用于治疗癌症患者，这些患者的癌细胞缺乏核苷或核苷碱基转运蛋白。
• Characterization of two putative prolinases (PepR1 and PepR2) from Lactobacillus plantarum WCFS1: Occurrence of two isozymes with structural similarity and different catalytic properties
  作者：Yanyu Huang、Takuji Tanaka

  DOI：10.1016/j.bbapap.2014.11.003

  日期：2015.2

  amino acid sequence identity (55.5% at the DNA level); however, PepR1 exhibits over 80% identity at the protein level with other lactobacilli prolinases while PepR2 exhibits only 51% or less identity. In this study, the putative genes were overexpressed in Escherichia coli, purified to gel electrophoretic homogeneity, and then characterized. Purified PepR1 and PepR2 hydrolysed Pro-Xaa dipeptide substrates

  植物乳杆菌WCSF1的两个推定的脯氨酸蛋白酶（PepR1和PepR2）具有48.5％的氨基酸序列同一性（在DNA水平上为55.5％）；然而，PepR1在蛋白质水平上与其他乳酸杆菌脯氨酸酶的同一性超过80％，而PepR2仅在51％或更少的同一性。在这项研究中，推定的基因在大肠杆菌中过表达，纯化至凝胶电泳均质，然后进行表征。纯化的PepR1和PepR2以相似的速率水解Pro-Xaa二肽底物，证明了它们作为脯氨酸酶的性质。使用圆二色性，动态光散射，凝胶过滤和分子模型进行的结构分析显示，两种蛋白酶均具有相似的结构特征：高β-折叠含量，同四聚体结构以及与PepI / PepL / PepR肽酶家族相似的折叠。然而，PepR1和PepR2的动力学和热力学分析表明，在许多方面存在差异：最佳温度（分别为25和30°C），最佳pH（分别为pH7.5和8.0），底物特异性（PepR2的高严格性），动力学参数，
• Human chorionic gonadotropin. III. Synthesis of a dotriacontapeptide corresponding to the C-terminal sequence 116-147 of the .BETA.-subunit of human chorionic gonadotropin (hCG).
  作者：KOICHI KAWASAKI、CHIYE KAWASAKI、YUKO TSUDA、MASAMI YAGYU、YOSHIO OKADA、KENJI YAMAJI、TETSU TAKAGI、OSAMU TANIZAWA

  DOI：10.1248/cpb.28.2699

  日期：——

  A dotriacontapeptide, H-Gln-Asp-Ser-Ser-Ser-Lys-Ala-Pro-Pro-Pro-Ser-Leu-Pro-Ser-Pro-Ser-Arg-Leu-Pro-Gly-Pro-Pro-Asn-Thr-Pro-Ile-Leu-Pro-Gln-Ser-Leu-Pro-OH, corresponding to the C-terminal sequence 116-147 of hCG-β proposed by Carlsen et al. was synthesized by stepwise fragment condensation, linking five fragments [Z-Gln-Asp(OBzl)-OH, Z-Ser(Bzl)-Ser-Ser-Lys(Boc)-NHNH2, Z-Ala-Pro-Pro-Pro-NHNHBoc, Z-Ser(Bzl)-Leu-Pro-NHNHBoc, and Z-Ser(Bzl)-Pro-Ser-NHNH2] to the hexadecapeptide reported in the preceding paper.

  通过分步片段缩合，将五个片段[Z-Gln-Asp(OBzl)-OH、Z-Ser(Bzl)-Ser-Ser-Lys(Boc)-NHNH2、Z-Ala-Pro-Pro-NHNHBoc、Z-Ser(Bzl)-Leu-Pro-NHNHBoc 和 Z-Ser(Bzl)-Pro-Ser-NHNH2]连接到前一篇论文中报告的十六肽上，合成了该化合物。