CAS: 14091-16-8; 4-(Trifluoromethyl)-Dl-Phenylalanine

该化合物是一种氨酸衍生物,其特点是有附于苯丙烯苯环的三氟甲基组,这种改变对其化学特性有重大影响,包括与标准苯丙烯相比,脂性增加和反应能力改变;三氟甲基组因其电子抽引效应而闻名,可能影响化合物在生物系统中的相互作用及其总体稳定性;作为Zwitter化合物,该物质具有酸性和基本特性,允许其参与各种生物化学反应;该物质在药用化学和药物设计中具有潜在用途,能够针对特定生物途径开发药品;此外,其独特的结构特征可能有助于其在影响蛋白折合体和功能方面的作用;

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114872-99-0 114873-07-3 114926-38-4

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2-oxo-3-(4-(trifluoromethyl)phenyl)propanoic acid (2,5)pyridophane(+/-)-15-aminomethyl-14-hydroxy-5,5-dimethyl-2,8-dithia9(2,5)pyridophane 2-acetamido-3-(4-(trifluoromethyl)phenyl)propanoic acid H-oxazol-5-one2-methyl-4-(4-trifluoromethyl-benzylidene)-4H-oxazol-5-one 2-Amino-3-(4-trifluoromethyl-phenyl)-propionic acid methyl ester; hydr°Chloride N-t-B°C-4-(trifluoromethyl)phenylalanine 3-(3,4-Dichloro-phenyl)-propane-1,2-diamine 3-(4-Trifluoromethyl-phenyl)-propane-1,2-diamine

合成工艺路线路线简述

    📜4-(Trifluoromethyl)-L-Phenylalanine置于pseudomonas Putida Phenylalanine Racemase体系中,化学反应生成4-三氟甲基-Dl-苯丙氨酸
    参考文献:苯丙氨酸解氨酶通过 Mio 辅因子非依赖性途径催化合成氨基酸
    标题:苯丙氨酸解氨酶通过 Mio 辅因子非依赖性途径催化合成氨基酸
    摘要:苯丙氨酸解氨酶 (Pal) 属于 4-亚甲基咪唑-5-酮 (Mio) 辅因子依赖性酶家族,其负责在真核生物和原核生物中将l-苯丙氨酸转化为反式肉桂酸.在高氨浓度条件下,这种脱氨反应是可逆的,因此人们对开发 Pal 作为非天然氨基酸的对映选择性合成的生物催化剂有相当大的兴趣.在此发现了一种以前未观测到的竞争性 Mio 非依赖性反应途径,该反应途径以非立体选择性方式进行并导致l-和d的产生描述了-苯丙氨酸衍生物.通过同位素标记研究和关键活性位点残基的诱变探索了 Mio 非依赖性途径的机制.获得的结果与通过逐步 E 1 Cb 消除机制发生的氨基酸脱氨基作用一致.
    Doi:10.1002/anie.201311061

    海关参考信息

    专利信息


    专利号:US-9938509-B2
    优先权日:2010-12-08
    标 题 :Biocatalysts and methods for the synthesis of armodafinil
    发明人:ANG EE LUI; ALVIZO OSCAR; BEHROUZIAN BEHNAZ; CLAY MICHAEL D; COLLIER STEVEN J; EBERHARD ELLEN D; FAN FU; SONG SHIWEI; SMITH DEREK J; WIDEGREN MAGNUS; WILSON ROBERT; XU JUNYE; ZHU JUN
    权利人:CODEXIS INC
    摘要:The present invention relates to non-naturally occurring polypeptides useful for preparing armodafinil, polynucleotides encoding the polypeptides, and methods of using the polypeptides. The non-naturally occurring polypeptides of the present invention are effective in carrying out biocatalytic conversion of the (i) 2-(benzhydrylsulfinyl)acetamide to (−)-2-[(R)-(diphenylmethyl)sulfinyl]acetamide (armodafinil), or (ii) benzhydryl-thioacetic acid to (R)-2-(benzhydrylsulfinyl)acetic acid, which is a pivotal intermediate in the synthesis of armodafinil, in enantiomeric excess.

    专利号:US-9663771-B2
    优先权日:2013-01-18
    标题 :Engineered biocatalysts useful for carbapenem synthesis
    发明人:SUKUMARAN JOLY; SMITH DEREK; YANG HONG; YEO WAN LIN; MOORE JEFFREY C
    权利人:CODEXIS INC
    摘要:The present disclosure provides engineered pNB esterase polypeptides useful for the synthesis of the carbapenem antibiotic, imipenem. The disclosure also provides polynucleotides encoding the engineered pNB esterases, host cells capable of expressing the engineered pNB esterases, and methods of using the engineered pNB esterases in the production of imipenem.

    专利号:US-2023391818-A1
    优先权日:2020-11-05
    标 题:Peptide synthesis method for suppressing defect caused by diketopiperazine formation
    发明人:NOMURA KENICHI; KAGE MIRAI; TAMIYA MINORU; KANAZAWA JUNICHIRO
    权利人:CHUGAI PHARMACEUTICAL CO LTD
    摘要:Solid-phase synthesis of a peptide has a problem that a desired elongation reaction is prevented from proceeding by diketopiperazine and a 6-membered diamine skeleton compound formed when a protective group at the N-terminal is removed. The present inventors have found that when in production of a peptide by a solid-phase method, a peptide in which an amino group at the N-terminal is protected with a protective group having an Fmoc skeleton is treated in a specific solvent with a base having a pKa of 23 or more in acetonitrile as a conjugate acid, and a peptide chain is then elongated, it is possible to solve the problem described above.

    专利号:US-12410410-B2
    优先权日:2015-02-10
    标题 :Ketoreductase polypeptides for the synthesis of chiral compounds
    发明人:ALVIZO OSCAR; AGARD NICHOLAS J; XIE XINKAI; ENTWISTLE DAVID; KOSJEK BIRGIT
    权利人:CODEXIS INC
    摘要:The present disclosure provides engineered ketoreductase enzymes having improved properties as compared to a naturally occurring wild-type ketoreductase enzyme. Also provided are polynucleotides encoding the engineered ketoreductase enzymes, host cells capable of expressing the engineered ketoreductase enzymes, and methods of using the engineered ketoreductase enzymes to synthesize a variety of chiral compounds.

    专利号:US-8932838-B2
    优先权日:2010-06-17
    标 题 :Biocatalysts and methods for the synthesis of (S)-3-(1-aminoethyl)-phenol
    发明人:CABIROL FABIEN LOUIS; GOHEL ANUPAM; OH SEONG HO; SMITH DEREK J; WONG BRIAN; LALONDE JAMES J
    权利人:CODEXIS INC
    摘要:The present disclosure provides engineered transaminase polypeptides having improved properties as compared to naturally occurring transaminases including the ability of converting the substrate, 3′-hydroxyacetophenone to (S)-3-(1-aminoethyl)-phenol in enantiomeric excess and high percentage conversion. Also provided are polynucleotides encoding the engineered transaminases, host cells capable of expressing the engineered transaminases, and methods of using the engineered transaminases to synthesize (S)-3-(1-aminoethyl)-phenol and related compounds useful in the production of active pharmaceutical ingredients.

    专利号:US-8932836-B2
    优先权日:2010-08-16
    标 题:Biocatalysts and methods for the synthesis of (1R,2R)-2-(3,4-dimethoxyphenethoxy)cyclohexanamine
    发明人:LIMANTO JOHN; BEUTNER GREGORY; GRAU BRENDAN; JANEY JACOB; KLAPARS ARTIS; ASHLEY ERIC R; STROTMAN HALLENA R; TRUPPO MATTHEW D; HUGHES GREGORY; CABIROL FABIEN; GOHEL ANUPAM; COLLIER STEVEN J; LIANG JACK; MOCK MARISSA; MUNDORFF EMILY; NOVICK SCOTT; SMITH DEREK
    权利人:LIMANTO JOHN; BEUTNER GREGORY; GRAU BRENDAN; JANEY JACOB; KLAPARS ARTIS; ASHLEY ERIC R; STROTMAN HALLENA R; TRUPPO MATTHEW D; HUGHES GREGORY; CABIROL FABIEN; GOHEL ANUPAM; COLLIER STEVEN J; LIANG JACK; MOCK MARISSA; MUNDORFF EMILY; NOVICK SCOTT; SMITH DEREK; CODEXIS INC
    摘要:The disclosure provides transaminase polypeptides capable of converting the substrate, 2-(3,4-dimethoxyphenethoxy)cyclohexanone to the trans diastereomer product (1R,2R)-2-(3,4-dimethoxyphenethoxy)cyclohexanamine in at least a 2:1 diastereomeric ratio relative to the cis diastereomer (1R,2S)-2-(3,4-dimethoxyphenethoxy)cyclohexanamine. The disclosure also provides polynucleotides, vectors, host cells, and methods of making and using the transaminase polypeptides in processes for preparing (1R,2R)-2-(3,4-dimethoxyphenethoxy)cyclohexanamine and its analogs, which can product compounds can be further used to prepare the aminocyclohexylether compound, (3R)-1-[(1R,2R)-2-[2-(3,4-dimethoxyphenyl)ethoxy]cyclohexyl]pyrrolidin-3-ol, which is an ion channel blocker.

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    合成参考文献


    参考文献:10.1016/j.bbrc.2012.01.069
    摘要:Ozawa K, Loscha KV, Kuppan KV, Loh CT, Dixon NE, Otting G. High-yield cell-free protein synthesis for site-specific incorporation of unnatural amino acids at two sites. Biochemical and Biophysical Research Communications. 2012 Feb;418(4):652–6. doi: 10.1016/j.bbrc.2012.01.069.
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