L-蛋氨酰-L-脯氨酸 | 59227-86-0

• 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-蛋氨酰-L-脯氨酸
• 英文名称: Met-Pro
• 英文别名: Met-Pro-OH；(2S)-1-[(2S)-2-amino-4-methylsulfanylbutanoyl]pyrrolidine-2-carboxylic acid
• CAS: 59227-86-0
• 化学式: C₁₀H₁₈N₂O₃S
• 分子量: 246.331
• InChiKey: DZMGFGQBRYWJOR-YUMQZZPRSA-N

物化性质

• 沸点：
  482.9±45.0 °C(Predicted)
• 密度：
  1.290±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  113
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

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

  (2S)-1-[(2S)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-4-(methylsulfanyl)butanoyl]pyrrolidine-2-carboxylic acid 在 哌啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 L-蛋氨酰-L-脯氨酸
  参考文献：
  名称：

  Functional Identification and Structure Determination of Two Novel Prolidases from cog1228 in the Amidohydrolase Superfamily,

  摘要：

  Two uncharacterized enzymes from the amidohydrolase superfamily belonging to cog1228 were cloned, expressed, and purified to homogeneity. The two proteins, Sgx9260c (gi|44242006) and Sgx9260b (gi|44479596), were derived from environmental DNA samples originating from the Sargasso Sea. The catalytic function and substrate profiles for Sgx9260c and Sgx9260b were determined using a comprehensive library of dipeptides and N-acyl derivative of L-amino acids. Sgx9260c catalyzes the hydrolysis of Gly-L-Pro, L-Ala-L-Pro, and N-acyl derivatives of L-Pro. The best substrate identified to date is N-acetyl-L-Pro with a value of k(cat)/K-m of 3 x 10(5) M-1 s(-1). Sgx9260b catalyzes the hydrolysis of L-hydrophobic L-Pro dipeptides and N-acyl derivatives of L-Pro. The best substrate identified to date is N-propionyl-L-Pro with a value of k(cat)/K-m of 1 x 10(5) M-1 s(-1). Three-dimensional structures of both proteins were determined by X-ray diffraction methods (PDB codes 3MKV and 3FEQ). These proteins fold as distorted (beta/alpha)(8)-barrels with two divalent cations in the active site. The structure of Sgx9260c was also determined as a complex with the N-methylphosphonate derivative of L-Pro (PDB code 3N2C). In this structure the phosphonate moiety bridges the binuclear metal center, and one oxygen atom interacts with His-140. The a-carboxylate of the inhibitor interacts with Tyr-231. The proline side chain occupies a small substrate binding cavity formed by residues contributed from the loop that follows beta-strand 7 within the (beta/alpha)(8)-barrel. A total of 38 other proteins from cog1228 are predicted to have the same substrate profile based on conservation of the substrate binding residues. The structure of an evolutionarily related protein, Cc2672 from Caulobacter crecentus, was determined as a complex with the N-methylphosphonate derivative of L-arginine (PDB code 3MTW).

  DOI：

  10.1021/bi100897u

文献信息

• SALTY TASTE ENHANCER
  申请人：T. HASEGAWA CO., LTD.

  公开号：US20160374380A1

  公开（公告）日：2016-12-29

  Provided is a salty taste enhancer that is capable of maintaining the flavor balance inherent in a food and enhancing salty taste despite a reduction in salt content. The salty taste enhancer effectively enhances salty taste by adding to a food or beverage having salty taste at least one selected from the group consisting of prolylglycine, glycylglycine, glycylproline and hydroxyprolylglycine, or a gelatin degradation product containing the dipeptide.
• US5167957A
  申请人：——

  公开号：US5167957A

  公开（公告）日：1992-12-01
• Chloroperoxidase-catalyzed oxidation of methionine derivatives
  作者：Herbert L Holland、Frances M Brown、Damian Lozada、Benjamin Mayne、W Rick Szerminski、Aaron J van Vliet

  DOI：10.1139/v02-025

  日期：2002.6.1

  Treatment of N-methoxycarbonyl C-carboxylate ester derivatives of L- and D-methionine and L-ethionine by chloroperoxidase–hydrogen peroxide resulted in oxidation at sulfur to produce the (R_S) sulfoxide in moderate to high diastereomeric excess. The (R_S) sulfoxide of methionine was also obtained in moderate to high diastereomeric excess from (±)_SO-N-methoxycarbonyl-L-methionine methyl ester sulfoxide by ester hydrolysis using α-chymotrypsin, Aspergillus sp. protease or subtilisin Carlsberg. Key words: amino acid oxidation, biocatalysis, biotransformation, chloroperoxidase, enzyme catalysis, lipase, sulfoxidation.

  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。
• Functional Identification and Structure Determination of Two Novel Prolidases from cog1228 in the Amidohydrolase Superfamily,
  作者：Dao Feng Xiang、Yury Patskovsky、Chengfu Xu、Alexander A. Fedorov、Elena V. Fedorov、Abby A. Sisco、J. Michael Sauder、Stephen K. Burley、Steven C. Almo、Frank M. Raushel

  DOI：10.1021/bi100897u

  日期：2010.8.10

  Two uncharacterized enzymes from the amidohydrolase superfamily belonging to cog1228 were cloned, expressed, and purified to homogeneity. The two proteins, Sgx9260c (gi|44242006) and Sgx9260b (gi|44479596), were derived from environmental DNA samples originating from the Sargasso Sea. The catalytic function and substrate profiles for Sgx9260c and Sgx9260b were determined using a comprehensive library of dipeptides and N-acyl derivative of L-amino acids. Sgx9260c catalyzes the hydrolysis of Gly-L-Pro, L-Ala-L-Pro, and N-acyl derivatives of L-Pro. The best substrate identified to date is N-acetyl-L-Pro with a value of k(cat)/K-m of 3 x 10(5) M-1 s(-1). Sgx9260b catalyzes the hydrolysis of L-hydrophobic L-Pro dipeptides and N-acyl derivatives of L-Pro. The best substrate identified to date is N-propionyl-L-Pro with a value of k(cat)/K-m of 1 x 10(5) M-1 s(-1). Three-dimensional structures of both proteins were determined by X-ray diffraction methods (PDB codes 3MKV and 3FEQ). These proteins fold as distorted (beta/alpha)(8)-barrels with two divalent cations in the active site. The structure of Sgx9260c was also determined as a complex with the N-methylphosphonate derivative of L-Pro (PDB code 3N2C). In this structure the phosphonate moiety bridges the binuclear metal center, and one oxygen atom interacts with His-140. The a-carboxylate of the inhibitor interacts with Tyr-231. The proline side chain occupies a small substrate binding cavity formed by residues contributed from the loop that follows beta-strand 7 within the (beta/alpha)(8)-barrel. A total of 38 other proteins from cog1228 are predicted to have the same substrate profile based on conservation of the substrate binding residues. The structure of an evolutionarily related protein, Cc2672 from Caulobacter crecentus, was determined as a complex with the N-methylphosphonate derivative of L-arginine (PDB code 3MTW).