CAS: 80126-53-0; H-Phe(2-Me)-Oh

该化合物是一种非天然的氨基酸衍生物,其特点是在苯环在苯丙氨的2位置上引入一个甲基组,这种改变会增加不育障碍,改变电子特性,使其在peptide合成和药用化学中具有价值,其结构独特性使得可以研究peptide的符合性和稳定性,特别是在设计受限制的类比或酶抑制剂时.该化合物通常用于研究应用中,需要量制成的氨基酸基,以调节生物活动或物理化学特性.高纯度等级确保与固相聚聚(SPS)和其他要求很高的合成议定书的兼容性.

结构式图片

相似化合物

22888-51-3 80126-54-1 114873-05-1

物理性质

MSDS等安全信息

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CAS号1111643-38-9 2-([(18)F]-fluo... | CAS号939-57-1 (E)-3-(邻甲苯基)丙烯酸 | CAS号80102-29-0 B°C-D-2-甲基苯丙氨酸

合成工艺路线路线简述

  • 合成目标产物 2-Methylphenyl-L-Alanine 主要起始原料 Dl-2'-Methylphenylalanine Hydrochloride
  • 5463-90-1 = 80126-53-0
    反应条件:1.1 Reagents: Ammonium Hydroxide Solvents: Dimethylformamide,Water; Ph 7,38 °C1.2 Catalysts: Amidase; 24 H,Ph 7,38 °C
    标题:Synthesis And Resolution Of N-Boc-2-Methyl-L-Phenylalanine,N-Boc-3-Methyl-L-Phenylalanine And N-Boc-4-Methyl-L-Phenylalanine Isomers
    作者:Li,Xiao-Hui; Et Al
    参考文献:Gaodeng Xuexiao Huaxue Xuebao 日期:2008 卷标:29(7) 页码:1363-1366]

    5440-53-9 = 80126-53-0
    反应条件:1.1 Reagents: Sodium Hydroxide Solvents: Ethanol,Water; 5 H,0 °C1.2 Reagents: Sodium Bicarbonate Solvents: Water2.1 Solvents: Toluene; 5 H,110 °C3.1 Reagents: Sodium Hydroxide Solvents: Ethanol,Water; 5 H,0 °C3.2 Reagents: Sodium Bicarbonate Solvents: Water4.1 Reagents: Ammonium Hydroxide Solvents: Dimethylformamide,Water; Ph 7,38 °C4.2 Catalysts: Amidase; 24 H,Ph 7,38 °C
    标题:Synthesis And Resolution Of N-Boc-2-Methyl-L-Phenylalanine,N-Boc-3-Methyl-L-Phenylalanine And N-Boc-4-Methyl-L-Phenylalanine Isomers
    作者:Li,Xiao-Hui; Et Al
    参考文献:Gaodeng Xuexiao Huaxue Xuebao 日期:2008 卷标:29(7) 页码:1363-1366]

    1068-90-2 = 80126-53-0
    反应条件:1.1 Reagents: Sodium Solvents: Ethanol; 30 H,110 °C1.2 5 H,110 °C2.1 Reagents: Sodium Hydroxide Solvents: Ethanol,Water; 5 H,0 °C2.2 Reagents: Sodium Bicarbonate Solvents: Water3.1 Solvents: Toluene; 5 H,110 °C4.1 Reagents: Sodium Hydroxide Solvents: Ethanol,Water; 5 H,0 °C4.2 Reagents: Sodium Bicarbonate Solvents: Water5.1 Reagents: Ammonium Hydroxide Solvents: Dimethylformamide,Water; Ph 7,38 °C5.2 Catalysts: Amidase; 24 H,Ph 7,38 °C
    标题:Synthesis And Resolution Of N-Boc-2-Methyl-L-Phenylalanine,N-Boc-3-Methyl-L-Phenylalanine And N-Boc-4-Methyl-L-Phenylalanine Isomers
    作者:Li,Xiao-Hui; Et Al
    参考文献:Gaodeng Xuexiao Huaxue Xuebao 日期:2008 卷标:29(7) 页码:1363-1366]

    80102-28-9 = 80126-53-0 + 114872-93-4
    反应条件:1.1 Reagents: Sodium Hydroxide,Carboxypeptidase A Solvents: Water
    标题:Synthesis,Resolution And Characterization Of Ring Substituted Phenylalanines And Tryptophans
    作者:Porter,John; Et Al
    参考文献:International Journal Of Peptide & Protein Research 日期:1987 卷标:30(1) 页码:13-21]

    939-57-1 = 80126-53-0 + 752198-38-2
    反应条件:1.1 Reagents: Ammonia Catalysts: Aminomutase,Phenylalanine 2,3- Solvents: Water; 24 H,Ph 10,30 °C1.2 5 Min,99 °C
    标题:Phenylalanine Aminomutase-Catalyzed Addition Of Ammonia To Substituted Cinnamic Acids: A Route To Enantiopure α- And β-Amino Acids
    作者:Szymanski,Wiktor; Et Al
    参考文献:Journal Of Organic Chemistry 日期:2009 卷标:74(23) 页码:9152-9157]

    22888-51-3 = 80126-53-0 + 114872-93-4
    反应条件:1.1 Reagents: Trifluoroacetic Anhydride Solvents: Trifluoroacetic Acid2.1 Reagents: Sodium Hydroxide,Carboxypeptidase A Solvents: Water
    标题:Synthesis,Resolution And Characterization Of Ring Substituted Phenylalanines And Tryptophans
    作者:Porter,John; Et Al
    参考文献:International Journal Of Peptide & Protein Research 日期:1987 卷标:30(1) 页码:13-21]

    2373-76-4 = 80126-53-0 [标题:Reaction Conditions
    标题:Synthesis Of L-Phenylalanine Analogs By Rhodotorula Glutinis. Bioconversion Of Cinnamic Acids Derivatives
    作者:Renard,G.; Et Al
    参考文献:Biotechnology Letters 日期:1992 卷标:14(8) 页码:673-8]

    61676-24-2 = 80126-53-0
    反应条件:1.1 Catalysts: Aspartate Aminotransferase
    标题:Application Of Escherichia Coli Aspartate Transaminase To Amino Acid Synthesis
    作者:Baldwin,Jack E.; Et Al
    参考文献:Tetrahedron Letters 日期:1987 卷标:28(32) 页码:3745-6]

    939-57-1 = 80126-53-0
    反应条件:1.1 Catalysts: Phenylalanine Ammonia-Lyase Solvents: Water; 16 H,Ph 10,30 °C1.2 Reagents: Methanol
    标题:Mapping The Hydrophobic Substrate Binding Site Of Phenylalanine Ammonia-Lyase From Petroselinum Crispum
    作者:Nagy,Emma Z. A.; Et Al
    参考文献:Acs Catalysis 日期:2019 卷标:9(9) 页码:8825-8834]

    141-82-2 + 529-20-4 = 80126-53-0
    反应条件:1.1 Catalysts: Piperidine Solvents: Pyridine; 6 H,80 °C; Cooled1.2 Reagents: Hydrochloric Acid Solvents: Water2.1 Catalysts: Phenylalanine Ammonia-Lyase Solvents: Water; 16 H,Ph 10,30 °C2.2 Reagents: Methanol
    标题:Mapping The Hydrophobic Substrate Binding Site Of Phenylalanine Ammonia-Lyase From Petroselinum Crispum
    作者:Nagy,Emma Z. A.; Et Al
    参考文献:Acs Catalysis 日期:2019 卷标:9(9) 页码:8825-8834]

    = 80126-53-0
    反应条件:1.1 Reagents: Sodium Hydroxide Solvents: Ethanol,Water; 5 H,0 °C1.2 Reagents: Sodium Bicarbonate Solvents: Water2.1 Reagents: Ammonium Hydroxide Solvents: Dimethylformamide,Water; Ph 7,38 °C2.2 Catalysts: Amidase; 24 H,Ph 7,38 °C
    标题:Synthesis And Resolution Of N-Boc-2-Methyl-L-Phenylalanine,N-Boc-3-Methyl-L-Phenylalanine And N-Boc-4-Methyl-L-Phenylalanine Isomers
    作者:Li,Xiao-Hui; Et Al
    参考文献:Gaodeng Xuexiao Huaxue Xuebao 日期:2008 卷标:29(7) 页码:1363-1366]

    = 80126-53-0
    反应条件:1.1 Solvents: Toluene; 5 H,110 °C2.1 Reagents: Sodium Hydroxide Solvents: Ethanol,Water; 5 H,0 °C2.2 Reagents: Sodium Bicarbonate Solvents: Water3.1 Reagents: Ammonium Hydroxide Solvents: Dimethylformamide,Water; Ph 7,38 °C3.2 Catalysts: Amidase; 24 H,Ph 7,38 °C
    标题:Synthesis And Resolution Of N-Boc-2-Methyl-L-Phenylalanine,N-Boc-3-Methyl-L-Phenylalanine And N-Boc-4-Methyl-L-Phenylalanine Isomers
    作者:Li,Xiao-Hui; Et Al
    参考文献:Gaodeng Xuexiao Huaxue Xuebao 日期:2008 卷标:29(7) 页码:1363-1366]

    5440-53-9 = 80126-53-0 + 114872-93-4
    反应条件:1.1 Reagents: Hydrogen Bromide Solvents: Water2.1 Reagents: Trifluoroacetic Anhydride Solvents: Trifluoroacetic Acid3.1 Reagents: Sodium Hydroxide,Carboxypeptidase A Solvents: Water
    标题:Synthesis,Resolution And Characterization Of Ring Substituted Phenylalanines And Tryptophans
    作者:Porter,John; Et Al
    参考文献:International Journal Of Peptide & Protein Research 日期:1987 卷标:30(1) 页码:13-21]

    1068-90-2 = 80126-53-0 + 114872-93-4
    反应条件:1.1 Reagents: Sodium Ethoxide Solvents: Ethanol1.2 Solvents: Ethanol1.3 Reagents: 2-Fluorobenzyl Bromide2.1 Reagents: Hydrogen Bromide Solvents: Water3.1 Reagents: Trifluoroacetic Anhydride Solvents: Trifluoroacetic Acid4.1 Reagents: Sodium Hydroxide,Carboxypeptidase A Solvents: Water
    标题:Synthesis,Resolution And Characterization Of Ring Substituted Phenylalanines And Tryptophans
    作者:Porter,John; Et Al
    参考文献:International Journal Of Peptide & Protein Research 日期:1987 卷标:30(1) 页码:13-21
Dl-2-甲基苯丙氨酸盐酸盐置于phenylalanine Ammonia Lyase From Lettuce (Lactuca Sativa L.) Lspal3,Ammonium Carbamate体系中,用 甲醇,水 作为反应溶剂,化学反应 1.33H,反应生成 L-2-甲基苯丙氨酸
参考文献:生菜 (Lactuca Sativa L.) 苯丙氨酸氨裂解酶作为生产 D-和 L-氨基酸的稳健生物催化剂的表征
标题:生菜 (Lactuca Sativa L.) 苯丙氨酸氨裂解酶作为生产 D-和 L-氨基酸的稳健生物催化剂的表征
摘要:苯丙氨酸解氨酶 (Pal) 催化l-苯丙氨酸可逆转化为相应的反式肉桂酸,从而提供了一条获得光学纯 α-氨基酸的途径.我们探索了生菜(Lactuca Sativa L.)基因组中编码的所有五种 Pal 的催化功能,此前已知这些 Pal 与伤口褐变有关.所有ls Pal 在氨消除反应中均对l-苯丙氨酸具有活性,并在 55-60 oc 和 Ph 9.0-9.5 时表现出最大活性.然而,其中的四种(Ls Pal1-Ls Pal4)表现出比ls Pal5 显着更高的活性和热稳定性,以及更广泛的底物谱,包括一些具有空间要求或给电子取代基的具有挑战性的底物.对最好的ls Pal3 进行了一组 21 种外消旋苯丙氨酸衍生物的动力学拆分,以及 21 种肉桂酸衍生物的氨加成.它在大多数情况下表现出优异的对映选择性,并且对于许多具有挑战性的非天然底物,其活性明显优于之前描述的 Pal,这证明了其在生物催化方面的巨大潜力.
DOI:10.1021/acs.Jafc.2C07890

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主要参考文献

[参考文献]: Luckose F, Et Al. Effects Of Amino Acid Derivatives On Physical, Mental, And Physiological Activities. Crit Rev Food Sci Nutr. 2015;55(13):1793-845.

合成参考文献


摘要:Faber, K.; Glueck, S. M., Science of Synthesis: Biocatalysis in Organic Synthesis, (2015) 1, 476.
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