CAS: 23239-35-2; (S)-2-Amino-2-Methyl-3-Phenylpropanoic Acid

该化合物是一种非蛋白性α-氨酸,其特点是一个手性中心和一个苯基组,使其成为制药和生化研究的宝贵中间体.它的立体结构使非对称合成和消毒剂设计的应用成为可能.该化合物的僵硬脊椎和疏水侧链有助于研究酶基相互作用和设计酶抑制剂.高纯度能确保研究应用的再生性.它在生理条件下的稳定性进一步增强了其对药用化学研究的适宜性.该化合物通常用于开发生物活性分子和作为新型治疗剂的构件.

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相似化合物

1132-26-9 17350-84-4 135944-05-7

欧盟法规

ECHA物质C&L通报

上下游产品

DL-N-Trifluoracetyl-α-methylphenylalanin methyl 2-(phenylmethyl)-2-aminopropionate α-methyl phenylalanine amide α-methyl-α-carbethoxy-β-phenethylamine B°C-L-α-Methylphenylvalin*Dicyclohexylamin ethyl (S)-2-amino-2-methyl-3-phenylpropionate B°C-D-(αMe)Phe-OH Ac-L-(αMe)Phe-OH oxazol-5(4H)-one

合成工艺路线路线简述

    📜(R)-(-)-2-Cyano-2-Methyl-3-Phenylpropionic Acid置于盐酸,Sodium Hydroxide,碘苯二乙酸,双氧水体系中,用 甲醇 用作溶剂,化学反应 7.0H,反应生成2-甲基-L-苯丙氨酸一水物
    参考文献:高效分离外消旋-2-氰基-2-甲基-3-苯基丙酸.大规模实验室规模对映体合成(S)-α-甲基苯丙氨酸的合适原料
    标题:高效分离外消旋-2-氰基-2-甲基-3-苯基丙酸.大规模实验室规模对映体合成(S)-α-甲基苯丙氨酸的合适原料
    摘要:已经开发了由苯甲醛和氰基乙酸甲酯合成(S)-α-甲基苯丙氨酸的大规模实验室规模.合成是基于以下顺序:(i)外消旋2-氰基-2-甲基-3-苯基丙酸的制备,(II)使用去甲麻黄碱通过结晶拆分对映异构体,以及(III)开发有效的对映收敛合成(的小号从对映体纯()-α甲基苯丙氨酸小号和(-)-[r)-2-氰基-2-甲基-3-苯基丙酸.实验程序的简单性,避免了低温反应,需要惰性气氛和柱色谱,再加上使用廉价且容易获得的试剂,使得该方法在合成上非常有吸引力.
    Doi:10.1016/s0957-4166(03)00450-6

    海关参考信息

    专利信息


    专利号:WO-9517903-A1
    优先权日:1993-12-28
    标 题:Modular design and synthesis of oxazolone-derived molecules
    发明人:HOGAN JOSEPH C JR; CASEBIER DAVID; FURTH PAUL; TU CHENG
    权利人:ARQULE PARTNERS L P; HOGAN JOSEPH C JR; CASEBIER DAVID; FURTH PAUL; TU CHENG
    摘要:The design and synthesis of novel oxazolone-derived molecular modules and the use of the modules in the construction of new molecules and fabricated materials is disclosed. The new molecules and fabricated materials are molecular recognition agents useful in the design and synthesis of drugs, and have applications in separations and materials science.

    专利号:US-2024218014-A1
    优先权日:2022-11-21
    标 题:Synthesis of a cyclic peptide
    发明人:BAUR PIUS BRUNO; CLEATOR EDWARD; DENIAU GILDAS; EISELE FRANK; FLÖGEL OLIVER; HUSTE ANJA; KEHL MARCEL ROMAN; LÖWENECK MARKUS; SILVA ROLANDO RAVELO; VORBERG RAFFAEL
    权利人:JANSSEN PHARMACEUTICA NV
    摘要:Processes for performing peptide synthesis, particularly for cyclic peptide synthesis are generally described. Reaction intermediates of the peptide synthesis are also described.

    专利号:US-2004101523-A1
    优先权日:1989-07-27
    标题:Renal-selective prodrugs for control of renal smpathetic nerve activity in the treatment of hypertension
    发明人:REITZ DAVID B; KOEPKE JOHN P; BLAINE EDWARD H; SCHUH JOSEPH R; MANNING ROBERT E; SMITS GLENN J
    权利人:SEARLE & CO
    摘要:Renal-selective prodrugs are described which are preferentially converted in the kidney to compounds capable of inhibiting synthesis of catecholamine-type neurotransmitters involved in renal sympathetic nerve activity. The prodrugs described herein are derived from inhibitor compounds capable of inhibiting one or more of the enzymes involved in catecholamine synthesis, such compounds being classifiable as tyrosine hydroxylase inhibitors, or as dopa-decarboxylase inhibitors, or as dopamine-β-hydroxylase inhibitors. These inhibitor compounds are linked to a chemical moiety, such as a glutamic acid derivative, by a cleavable bond which is recognized selectively by enzymes located predominantly in the kidney. The liberated inhibitor compound is then available in the kidney to inhibit one or more of the enzymes involved in catecholamine synthesis. Inhibition of renal catecholamine synthesis can suppress heightened renal nerve activity associated with sodium-retention related disorders such as hypertension. Conjugates of particular interest are glutamyl derivatives of dopamine-β-hydroxylase inhibitors, of which N-acetyl-γ-glutamyl fusaric acid hydrazide (shown below) is preferred.

    专利号:WO-9101724-A1
    优先权日:1989-07-27
    标题 :Renal-selective prodrugs for the treatment of hypertension
    发明人:REITZ DAVID B; KOEPKE JOHN P; BLAINE EDWARD H; SCHUH JOSEPH R; MANNING ROBERT E; SMITS GLENN J
    权利人:SEARLE & CO
    摘要:Renal-selective prodrugs are described which are preferentially converted in the kidney to compounds capable of inhibiting synthesis of catecholamine-type neurotransmitters involved in renal sympathetic nerve activity. The prodrugs described herein are derived from inhibitor compounds capable of inhibiting one or more of the enzymes involved in catecholamine synthesis, such compounds being classifiable as tyrosine hydroxylase inhibitors, or as depa-decarboxylase inhibitors, or as dopamine-β-hydroxylase inhibitors. These inhibitors compounds are linked to a chemical moiety, such as a glutamic acid derivative, by a cleavable bond which is recognized selectively by enzymes located predominantly in the kidney. The liberated inhibitor compound is then available in the kidney to inhibit one or more of the enzymes involved in catecholamine synthesis. Inhibition of renal catecholamine synthesis can suppress heightened renal nerve activity associated with sodium-retention related disorders such as hypertension. Conjugates of particular interest are glutamyl derivatives of dopamine-β-hydroxylase inhibitors, of which N-acetyl-Y-glutamyl fusaric acid is preferred.

    专利号:WO-9201667-A1
    优先权日:1990-07-25
    标题 :Renal-selective prodrugs for control of renal sympathetic nerve activity in the treatment of hypertension
    发明人:REITZ DAVID B; KOEPKE JOHN P; BLAINE EDWARD H; SCHUH JOSEPH R; MANNING ROBERT E; SMITS GLENN J
    权利人:SEARLE & CO
    摘要:Renal-selective prodrugs are described which are preferentially converted in the kidney to compounds capable of inhibiting synthesis of catecholamine-type neurotransmitters involved in renal sympathetic nerve activity. The prodrugs described herein are derived from inhibitor compounds capable of inhibiting one or more of the enzymes involved in catecholamine synthesis, such compounds being classifiable as tyrosine hydroxylase inhibitors, or as dopa-decarboxylase inhibitors, or as dopamine-β-hydroxylase inhibitors. These inhibitor compounds are linked to a chemical moiety, such as a glutamic acid derivative, by a cleavable bond which is recognized selectively by enzymes located predominantly in the kydney. The liberated inhibitor compound is then available in the kidney to inhibit one or more of the enzymes involved in catecholamine synthesis. Inhibition of renal catecholamine synthesis can suppress heightened renal nerve activity associated with sodium-retention related disorders such as hypertension. Conjugates of particular interest are glutamyl derivatives of dopamine-β-hydroxylase-inhibitors, of which N-acetyl-η-glutamyl fusaric acid hydrazide [represented in formula (a)] is preferred.

    专利号:US-10526379-B2
    优先权日:2015-06-05
    标题:Methods and products for fusion protein synthesis
    发明人:HOWARTH MARK
    权利人:UNIV OXFORD INNOVATION LTD
    摘要:A method of producing a fusion protein is provided. The method includes: a) contacting a first protein with a second protein under conditions that enable the formation of an isopeptide bond between said proteins to form a linked protein; and b) contacting the linked protein from (a) with a third protein under conditions that enable the formation of an isopeptide bond between said third protein and said linked protein to form a fusion protein. Peptide linkers and the use of orthogonal pairs of said linkers in the synthesis of fusion proteins are also provided. Recombinant proteins comprising said linkers, nucleic acid molecules encoding said proteins and linkers, vectors comprising said nucleic acid molecules and host cells comprising said vectors and nucleic acid molecules are also contemplated.

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    品牌试剂参考报价(招募中)

    📌 第三方产品分析报告

    ✅ COA系统入驻 | 共享模式

    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):1793-826.
    [参考文献]: A T Wyse, Et Al. Alanine Prevents The Decrease Of Na+,K+-Atpase Activity In Experimental Phenylketonuria. Metab Brain Dis. 1999 Jun;14(2):95-101.
    [参考文献]: A T Wyse, Et Al. Effect Of Phenylalanine And Its Metabolites On Atp Diphosphohydrolase Activity In Synaptosomes From Rat Cerebral Cortex. Neurochem Res. 1994 Sep;19(9):1175-80.
    [参考文献]: Elisa Costabeber, Et Al. Hyperphenylalaninemia Reduces Creatine Kinase Activity In The Cerebral Cortex Of Rats. Int J Dev Neurosci. 2003 Apr;21(2):111-6.
    [参考文献]: M Castillo, Et Al. Effect Of Experimental Hyperphenylalaninemia Induced By Dietary Phenylalanine Plus Alpha-Methylphenylalanine Administration On Amino Acid Concentration In Neonatal Chick Brain, Plasma, And Liver. Neurochem Res. 1988 Jun;13(6):547-50.

    合成参考文献


    摘要:Hall, M.; Faber, K.; Tasnádi, G., Science of Synthesis: Biocatalysis in Organic Synthesis, (2015) 1, 307.
    摘要:Hall, M.; Faber, K.; Tasnádi, G., Science of Synthesis: Biocatalysis in Organic Synthesis, (2015) 1, 310.
    参考文献:10.1007/s11030-005-8112-3
    摘要:Thierry B, Plaquevent JC, Cahard D. Cinchona alkaloid-based polymer-bound phase-transfer catalysts: efficient enantioselective alkylation of benzophenone imine of glycine esters. Mol Divers. 2005;9(4):277–90. doi: 10.1007/s11030-005-8112-3.
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