L-脯氨酰-L-蛋氨酸 | 52899-08-8

• 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
• 中文名称: L-脯氨酰-L-蛋氨酸
• 英文名称: prolyl-methionine
• 英文别名: Pro-Met；PM；L-Pro-L-Met；L-Prolyl-L-methionine；(2S)-4-methylsulfanyl-2-[[(2S)-pyrrolidine-2-carbonyl]amino]butanoic acid
• CAS: 52899-08-8
• 化学式: C₁₀H₁₈N₂O₃S
• 分子量: 246.331
• InChiKey: MTWJTFBVRDGROD-YUMQZZPRSA-N

物化性质

• 沸点：
  530.5±50.0 °C(Predicted)
• 密度：
  1.232±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：
  0.8
• 拓扑面积：
  111
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2933990090

制备方法与用途

H-Pro-Met-OH 是一种含有脯氨酸和蛋氨酸的二肽，可作为脯氨酸酶的底物，并且也被用于多肽的合成。[1][2]

反应信息

• 作为反应物：
  描述：

  L-脯氨酰-L-蛋氨酸 在 盐酸 、 sodium hydroxide 作用下， 反应 12.0h， 生成 N-MOC-Pro-Met-OMe
  参考文献：
  名称：

  Chloroperoxidase-catalyzed oxidation of methionine derivatives

  摘要：

  氯过氧化酶-过氧化氢对N-甲氧羰基C-羧酸酯衍生物的L-和D-蛋氨酸以及L-依氨酸进行处理，导致硫原子氧化产生(RS)亚硫氧化物，其对映异构体过量为中等到高。甲硫氧化物也可通过α-胰蛋白酶、曲霉孢蛋白酶或卡尔斯堡亚硫酸酯水解从(±)SO-N-甲氧羰基-L-蛋氨酸甲酯亚硫酸酯中以中等到高的对映异构体过量获得。关键词：氨基酸氧化、生物催化、生物转化、氯过氧化酶、酶催化、脂肪酶、亚硫氧化。

  DOI：

  10.1139/v02-025
• 作为产物：
  描述：

  tert-butyl (2S)-2-[[(2S)-1-methoxy-4-methylsulfanyl-1-oxobutan-2-yl]carbamoyl]pyrrolidine-1-carboxylate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 L-脯氨酰-L-蛋氨酸
  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

文献信息

• ˙OH radical induced decarboxylation of methionine-containing peptides. Influence of peptide sequence and net charge
  作者：Krzysztof Bobrowski、Christian Schöneich、Jerzy Holcman、Klaus-Dieter Asmus

  DOI：10.1039/p29910000353

  日期：——

  The ˙OH radical induced oxidation of methionine-containing peptides results in significantly different decarboxylation yields upon variation of the location of the methionine unit with respect to the terminal functions (Met–Gly, Met–Glu, Met–Gly–Gly, Gly–Met–Gly, Gly–Met and Gly–Gly–Met), or with the nature of neighbouring amino acids located at the N-terminus of methionine (Ala–Met, β-Ala-Met, Val-Met

  ˙OH自由基诱导的含蛋氨酸肽的氧化会导致蛋氨酸单元位置相对于末端功能（Met–Gly，Met–Glu，Met–Gly–Gly，Gly–Met -Gly，Gly-Met和Gly-Gly-Met），或具有位于蛋氨酸N-末端的相邻氨基酸（Ala-Met，β-Ala-Met，Val-Met，Leu-Met，Ser -Met，Thr-Met，His-Met，γ-Glu-Met，Pro-Met，Gly-Gly-Phe-Met和Tyr-Gly-Gly-Phe-Met）。γ-射线分解测得的CO 2产率从0％（Met–Gly，Met–Glu，Met–Gly–Gly，Gly–Met–Gly和Pro–Met）变化到约80％（γ–Glu–Met）可用的˙OH自由基。从机理上讲，脱羧被认为是通过分子内“外层”电子从甲硫氨酸羧酸盐官能团转移到氧化硫官能团S˙ +。γ-Glu-Met中存在一条额外的N末端脱羧途径，该途
• 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，
• MUTANT PROTEIN HAVING THE PEPTIDE-SYNTHESIZING ACTIVITY
  申请人：ABE Isao

  公开号：US20070292916A1

  公开（公告）日：2007-12-20

  The present invention aims at providing an excellent peptide-synthesizing protein and a method for efficiently producing a peptide. The peptide is synthesized by reacting an amine component and a carboxy component in the presence of at least one of proteins shown in the following (I) and (II). (I) The mutant protein having an amino acid sequence comprising one or more mutations from any of the mutations 1 to 68, and the mutations 239 to 290 and 324 to 377 in an amino acid sequence of SEQ ID NO:2. (II) The mutant protein having an amino acid sequence comprising one or more mutations from any of the mutations L1 to L335 and M1 to M642 in an amino acid sequence of SEQ ID NO:208

  本发明旨在提供一种优秀的肽合成蛋白质及高效生产肽的方法。在以下（I）和（II）所示的蛋白质的至少一种存在下，通过在胺组分和羧组分存在下反应合成肽。其中，（I）为突变蛋白质，其氨基酸序列包括来自于突变1至突变68、突变239至突变290和突变324至突变377的一个或多个突变；（II）为突变蛋白质，其氨基酸序列包括来自于L1至L335和M1至M642的一个或多个突变。
• Mutant protein having the peptide-synthesizing activity
  申请人：Abe Isao

  公开号：US20070190602A1

  公开（公告）日：2007-08-16

  The present invention aims at providing an excellent peptide-synthesizing protein and a method for efficiently producing a peptide. The peptide is synthesized by reacting an amine component and a carboxy component in the presence of at least one of proteins shown in the following (I) and (II). (I) The mutant protein having an amino acid sequence comprising one or more mutations from any of the mutations 1 to 68, and the mutations 239 to 290 and 324 to 377 in an amino acid sequence of SEQ ID NO:2. (II) The mutant protein having an amino acid sequence comprising one or more mutations from any of the mutations L1 to L335 and M1 to M642 in an amino acid sequence of SEQ ID NO:208

  本发明旨在提供一种优异的合成肽蛋白质及高效生产肽的方法。在以下(I)和(II)所示的蛋白质的存在下，通过反应胺组分和羧基组分来合成肽。(I)突变蛋白质的氨基酸序列包括来自突变1到68和突变239到290以及SEQ ID NO:2的氨基酸序列中的突变324到377中的一个或多个突变。(II)突变蛋白质的氨基酸序列包括来自突变L1到L335和M1到M642和SEQ ID NO:208的氨基酸序列中的一个或多个突变。
• MUTANT PROTEIN HAVING PEPTIDE-PRODUCTION ACTIVITY
  申请人：Ajinomoto Co., Inc.

  公开号：EP1829968A1

  公开（公告）日：2007-09-05

  The present invention aims at providing an excellent peptide-synthesizing protein and a method for efficiently producing a peptide. The peptide is synthesized by reacting an amine component and a carboxy component in the presence of at least one of proteins shown in the following (I) and (II). (I) The mutant protein having an amino acid sequence comprising one or more mutations from any of the mutations 1 to 68, and the mutations 239 to 290 and 324 to 377 in an amino acid sequence of SEQ ID NO:2. (II) The mutant protein having an amino acid sequence comprising one or more mutations from any of the mutations L1 to L335 and M1 to M642 in an amino acid sequence of SEQ ID NO:208

  本发明旨在提供一种优良的多肽合成蛋白和一种高效生产多肽的方法。该多肽是在至少一种如下(I)和(II)所示的蛋白质存在下，通过胺组分和羧基组分反应合成的。 (I)突变体蛋白质，其氨基酸序列包含 SEQ ID NO:2 的氨基酸序列中的突变 1 至 68、突变 239 至 290 和突变 324 至 377 中的一个或多个突变。 (II)突变体蛋白质，其氨基酸序列包含以下突变中的一个或多个突变 SEQ ID NO:208 的氨基酸序列中的 L1 至 L335 突变和 M1 至 M642 突变中的任一个或多个突变的突变体蛋白。

表征谱图