脯氨酰-亮氨酸 | 52899-07-7

• 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
• 中文名称: 脯氨酰-亮氨酸
• 英文名称: L-prolyl-L-leucine
• 英文别名: Pro-Leu；prolylleucine；proline-leucine；(2S)-4-methyl-2-[[(2S)-pyrrolidin-1-ium-2-carbonyl]amino]pentanoate
• CAS: 52899-07-7
• 化学式: C₁₁H₂₀N₂O₃
• 分子量: 228.291
• InChiKey: ZKQOUHVVXABNDG-IUCAKERBSA-N

物化性质

• 熔点：
  253-255℃
• 沸点：
  457.5±45.0 °C(Predicted)
• 密度：
  1.126±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.4
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  78.4
• 氢给体数：
  3
• 氢受体数：
  4

安全信息

• WGK Germany：
  3

反应信息

• 作为反应物：
  描述：

  脯氨酰-亮氨酸 在 sodium ethanolate 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 72.25h， 生成 (2S)-1-acetyl-N-[(2S)-4-methyl-1-(morpholin-4-yl)-1-oxopentan-2-yl]pyrrolidine-2-carboxamide
  参考文献：
  名称：

  脯氨酰亮氨酸酰胺的酰基衍生物的合成

  摘要：

  提出了脯氨酰亮氨酰胺，N-苄基（脯氨酰）亮氨酰胺和N-（脯氨酰-亮氨酰）吗啉的合成途径。在三乙胺的存在下用苯甲酰氯或乙酰氯处理这些化合物，得到相应的（N-酰基烷基）亮氨酰胺。N-苄基（脯氨酰基）-亮氨酸酰胺的酰基衍生物和N-（脯氨酰基-亮氨酰）吗啉还通过在N存在下将（N-苯甲酰基脯氨酰基）-亮氨酸或（N-乙酰基脯氨酰）亮氨酸与苄胺或吗啉缩合而合成N'-二环己基-碳二亚胺。

  DOI：

  10.1134/s1070428020010145
• 作为产物：
  描述：

  Boc-Pro-Leu-OMe 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 脯氨酰-亮氨酸
  参考文献：
  名称：

  Chemical Characterization of Diketopiperazines in Beer

  摘要：

  Diketopiperazines (DKPs) corresponding to cyclic dipeptides have been detected in a variety of natural products as well as in processed foods, beverages, and food and beverage ingredients. A series of seven proline-based diketopiperazines, namely, cyclo(Ala-Pro), cyclo(Val-Pro), cyclo(Ile-Pro), cyclo(Leu-Pro), cyclo(Met-Pro), cyclo(Phe-Pro), and cyclo(Pro-Pro), has now been identified in beer. A marketplace cross-section of five commercial beers was studied, involving products manufactured in different countries using distinctly different raw materials and brewing styles; maximum concentrations of individual diketopiperazines in various beers ranged from below detection limit to approximately 24 ppm. The flavor characteristics of these compounds were described variously as bitter, mouth coating, drying, astringent, salty, metallic, and grainy when evaluated in water at concentrations ranging fi om 10 to 50 ppm. However, it is questionable whether or not the diketopiperazines reported here make a significant contribution to either the aroma or taste of most beers.

  DOI：

  10.1021/jf9700992
• 作为试剂：
  描述：

  丙酮 、 丙酮醛 在 脯氨酰-亮氨酸 作用下， 以 水 为溶剂， 反应 68.0h， 生成 3-hydroxyhexane-2,5-dione 、 3-hydroxyhexane-2,5-dione
  参考文献：
  名称：

  Organocatalysis with endogenous compounds: Towards novel non-enzymatic reactions

  摘要：

  The aldol reaction of the endogeneous compounds acetone and methylglyoxal has been studied using organocatalysis in relation to biologically relevant non-enzymatic reactions. Under preparative conditions, 3-hydroxy-2,5-hexadione, known as Henze's ketol, is formed in high yield and with enantioselectivities up to 88% ee. Furthermore, Henze's ketol is also formed under simulated physiological conditions at micromolar scale, indicating that this reaction might take place in living organisms. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.03.128

文献信息

• Catalytic, One-Pot Synthesis of β-Amino Acids from α-Amino Acids. Preparation of α,β-Peptide Derivatives
  作者：Carlos Saavedra、Rosendo Hernández、Alicia Boto、Eleuterio Álvarez

  DOI：10.1021/jo9004487

  日期：2009.7.3

  The one-pot conversion of readily available α-amino acid into β-amino acid derivatives was carried out in good yields. The method is a sequential process initiated by a tandem radical decarboxylation−oxidation reaction; the resulting acyliminium ion was trapped by silyl ketenes. Stoichiometric and catalytic versions of this reaction were developed and then applied to prepare modified di- and tripeptides

  容易获得的α-氨基酸一锅转化为β-氨基酸衍生物的收率很高。该方法是由串联自由基脱羧氧化反应引发的顺序过程。所得的丙烯酰亚胺离子被甲硅烷基烯酮捕获。开发了该反应的化学计量和催化形式，然后用于制备修饰的二肽和三肽。有趣的是，一些三肽在固态下形成了扩展的β-转角。
• Synthesis and conformation of n-trityl dipeptide derivatives
  作者：J. Matsoukas、Th. Tsegenidis、P. Cordopatis、D. Theodoropoulos

  DOI：10.1016/s0040-4020(01)91142-1

  日期：1984.1

  N-Tritylamino acids activated with DCC/HOBt, were coupled with various amino acid derivatives without racemization. The trityl group was split off quantitatively in 10% CCl3COOH monohydrate or CH2ClCOOH in CH2Cl2. Under these conditions detritylation of N-Trt-Trp-Gly-NH2 proceeds without formation of an oxindole derivative and side alkylation products, even in the absence of a scavenger. Dipeptide

  用DCC / HOBt活化的N-三苯甲基氨基酸与各种氨基酸衍生物偶联而没有外消旋作用。在10％CCl 3 COOH一水合物或CH 2 Cl 2中的CH 2 ClCOOH中将三苯甲基定量分离。在这些条件下，即使不存在清除剂，N-Trt-Trp-Gly-NH 2的去三苯甲基化反应也不会形成羟吲哚衍生物和副烷基化产物。二肽衍生物1和2表现出磁不对称性，归因于空间因素。
• Thioester-isocyanides: versatile reagents for the synthesis of cycle–tail peptides
  作者：Benjamin H. Rotstein、David J. Winternheimer、Lois M. Yin、Charles M. Deber、Andrei K. Yudin

  DOI：10.1039/c2cc16027g

  日期：——

  A novel class of reagents, thioester isocyanides, have been prepared and applied in the synthesis of peptide macrocycles. The isocyanide part of the molecule is deployed in a multicomponent macrocyclization step. This step is followed by chemoselective peptide ligation at the thioester part of the macrocycle. Our method can now be used for rapid assembly and evaluation of cycle–tail peptides.

  一种新型试剂，硫酯异氰酸酯，已经被合成并应用于肽大环的合成。分子的异氰酸酯部分在多组分大环化步骤中被使用。此步骤之后是对大环的硫酯部分进行化学选择性肽连接。我们的方法现在可以用于快速组装和评估环-尾肽。
• 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，