CAS: 19883-77-3; 3-Fluoro-L-Phenylalanine

该化合物是一种氨酸衍生物,其特点是在苯环相对于氨基组的元体位置上存在氟原子;该化合物是L-苯-亚麻尼的氟化类似物,是细胞合成蛋白的20种标准氨基酸之一;引入氟-亚麻尼可影响化合物的生化特性,如其疏水性,消毒效应以及与酶和受体的潜在相互作用. 3-氟-L-苯-亚麻尼经常用于研究,特别是与蛋白质结构和功能有关的研究以及药品的开发,其独特性能还可能使其在药物设计中使用,其中氟化合物可以增强代谢稳定性和生物利用率.与许多氟化合物一样,必须注意处理和处置可能对环境和健康造成的影响.

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相似化合物

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CAS号1866-38-2 间氯肉桂酸 | CAS号56-40-6 甘氨酸 | CAS号456-41-7 3-氟苄溴 | CAS号64493-16-9 2-氨基-3-(3-氟苯基)丙... | CAS号453-82-7 N-acetyl-3-fluo... | CAS号456-88-2 3-氟-DL-苯丙氨酸 | CAS号380-70-1 diethyl α-aceta... | CAS号17607-28-2 N-乙酰基-3-氟-DL-苯丙氨酸 | CAS号114873-01-7 B°C-L-3-氟苯丙氨酸

合成工艺路线路线简述

    3-氟肉桂酸置于ammonium Hydroxide,二氧化碳体系中,用 二甲基亚砜 用作溶剂,化学反应 12.0H,以99%的收率获得
    参考文献:伸缩一锅缩合氢化胺化策略,由苯甲醛合成光学纯的l-苯丙氨酸
    标题:伸缩一锅缩合氢化胺化策略,由苯甲醛合成光学纯的l-苯丙氨酸
    摘要:从商业上可买到的便宜的取代苯甲醛开始,设计了一种化学酶促伸缩方法,以高产率和光学纯度合成l-芳基丙氨酸.该方法利用化学的knoevenagel-Doebner缩合(使用微波辐照在短的反应时间内进行优化,以实现完全转化)和生物催化的苯丙氨酸氨裂合酶介导的加氢胺化反应(用于立体选择性地添加氨).这两个反应可以在一个罐中依次进行,从而将化学和生物催化的优点结合在一起.制备了五个相关的l-二卤代苯丙氨酸(71-84%收率,98-99%ee)作为分子探针,可用于药物化学和合成药物成分,证明了其制备性适用性.
    Doi:10.1016/j.Tet.2015.12.063

    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-10087221-B2
    优先权日:2013-03-21
    标题 :Synthesis of hydantoin containing peptide products
    发明人:HENKEL BERND
    权利人:SANOFI AVENTIS DEUTSCHLAND
    摘要:The present invention relates to a method of synthesizing a peptide product comprising at least one hydantoin group. The peptide product may be used as a reference material for the quality control of pharmaceutical peptides, particularly for the quality control of exendin peptides. Further, the invention relates to hydantoin building blocks, a method for manufacturing such building blocks and their use for the synthesis of peptide products.

    专利号:US-5554753-A
    优先权日:1993-08-25
    标 题:Catalytic enantioselective synthesis of α-amino acid derivatives by phase-transfer catalysis
    发明人:O'DONNELL MARTIN J; WU SHENGDE; ESIKOVA IRENA; MI AIQIAO
    权利人:INDIANA UNIVERSITY FOUNDATION
    摘要:Described are improved processes for the enantioselective synthesis of α-amino acids which involve combinations of solvents, highly-mixed and low-temperature reaction conditions, and novel catalysts. Also described are novel catalysts and precursors to α-amino acid derivatives.

    专利号:US-2023212788-A1
    优先权日:2020-03-26
    标 题:New method for automated on-demand biomolecular array synthesis
    发明人:ZHANG YIXIN; LIN WEILIN
    权利人:UNIV DRESDEN TECH
    摘要:The invention provides an amphiphilic coating for the direct and rapid synthesis of an array of peptides and small molecular compounds on a planar surface of a solid support, comprising a hydrophilic chemical structure and a lipophilic group, wherein said peptides and small molecular compounds differ from spot to spot from each other in the chemical structure, characterized in that said amphiphilic coating possesses low wettability to polar aprotic solvents used in the array synthesis; said amphiphilic coating possessing low wettability is designed that it can be converted to a coating possessing high wettability by hydrolysis of the lipophilic group; and said amphiphilic coating comprises an amino group for the reaction with an electrophilic reagent. The invention further provides a solid support comprising said amphiphilic coating and a method for method for the direct and rapid synthesis of an array of peptides and small molecular compounds on a planar surface of a solid support, wherein said planar surface of a solid support comprises said amphiphilic coating. Said method includes the enhancing of the wettability of a glass surface to organic solvents to realize automated on-demand biomolecular array synthesis comprising both, peptides and small molecular compounds. The amphiphilic surface can be switched to a hydrophilic surface, resulting in high density arrays suitable for protein- and cell-based screening.

    专利号:US-2003180804-A1
    优先权日:2001-10-29
    标题:Solid phase synthesis of chemical libraries
    发明人:PRYOR KENT E; LEWIS RONALD D; BROWN JASON W
    权利人:CORVAS INT INC
    摘要:The present invention provides compounds and compound libraries that are useful as protease modulators. The compounds and compound libraries are preferably made using the methods of the present invention which utilize peptide synthesis and combinatorial chemistry methods on a solid phase.

    专利号:US-12378290-B2
    优先权日:2019-09-05
    标题:Method for protein nanowire synthesis and tunable control of nanowire length
    发明人:REGUERA GEMMA; COSERT KRISTA MARIE
    权利人:UNIV MICHIGAN STATE
    摘要:Methods for synthesizing nanowires are provided. Modified PilA peptides are used as peptide building blocks for synthesizing the nanowires. The method places the peptide building blocks in an assembly buffer with a hydrophobe. Addition of a hydrophobe and molecular crowding by evaporation of the assembly buffer triggers the self-assembly of the peptide building blocks into fibers. Multiple elongation cycles of addition of peptide building blocks, mixing and evaporation are conducted to promote elongation of the fibers and synthesis of nanowires. Electronic characterization of the synthesized nanowires is provided.
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    主要参考文献

    [参考文献]: C Lian, Et Al. Fluorine-19 Nuclear Magnetic Resonance Spectroscopic Study Of Fluorophenylalanine- And Fluorotryptophan-Labeled Avian Egg White Lysozymes. Biochemistry. 1994 May 3;33(17):5238-45.
    [参考文献]: D H Young, Et Al. Fungitoxicity Of M-Fluorophenylalanine-Containing Peptides Towards Pythium Ultimum. Experientia. 1989 Apr 15;45(4):325-7.
    [参考文献]: Kinjal Rajesh Mehta, Et Al. Modulating Substrate Specificity Of Histone Acetyltransferase With Unnatural Amino Acids. Mol Biosyst. 2011 Nov;7(11):3050-5.
    [参考文献]: M G Hinds, Et Al. 19F N.M.R. Studies Of Conformational Changes Accompanying Cyclic Amp Binding To 3-Fluorophenylalanine-Containing Cyclic Amp Receptor Protein From Escherichia Coli. Biochem J. 1992 Oct 15;287 ( Pt 2)(Pt 2):627-32.
    [参考文献]: M J Fiske, Et Al. Hidden Overflow Pathway To L-Phenylalanine In Pseudomonas Aeruginosa. J Bacteriol. 1983 May;154(2):623-31.

    合成参考文献


    摘要:Nguyen, B. N.; Hii, K. K.; Szymański, W.; Janssen, D. B., Science of Synthesis: Stereoselective Synthesis, (2011) 1, 643.
    摘要:Bartsch, S.; Vogel, A., Science of Synthesis: Biocatalysis in Organic Synthesis, (2015) 2, 302.
    摘要:Parmeggiani, F.; Galman, J. L.; Montgomery, S. L.; Turner, N. J., Science of Synthesis, (2019) , 408.
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