CAS: 31105-91-6; (S)-2-Amino-3-(3,5-Difluorophenyl)Propanoic Acid

该化合物是一种氨基酸衍生物,其特点是,在L-苯麻拉尼苯环的3和5个位置上有两个氟原子替换替代物,这种改变会影响化合物的生化特性,例如其疏水性和与生物系统的相互作用;氟原子的存在往往会增强分子的稳定性和亲脂性,从而影响分子的溶性及生物膜的渗透性. 3,5-二氟-L-苯麻拉尼对药用化学和生物化学,特别是蛋白质结构和功能的研究以及药品的设计很感兴趣,其独特性还可能使它成为发展酶抑制剂或探索代谢途径的有用工具.与许多氟化化合物一样,仔细考虑其环境影响和生物影响对于研究和应用至关重要.

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CAS号84315-23-1 3,5-二氟苯乙烯酸 | CAS号266360-52-5 N-乙酰基-3-(3,5-二氟... | CAS号141776-91-2 3,5-二氟苄溴 | CAS号266360-46-7 diethyl 2-aceta... | CAS号205445-52-9 N-B°C-L-3,5-二氟苯丙氨酸

合成工艺路线路线简述

    3,5-二氟丁二酸置于petroselinum Crispum Phenylalanine Ammonialyase (1U) Ammonium Hydroxide体系中,化学反应 24.0H,以69%的收率获得产物l-3,5-二氟苯丙氨酸
    参考文献:Phenylalanine Ammonia-Lyase: The Use Of Its Broad Substrate Specificity For Mechanistic Investigations And Biocatalysis-synthesis Ofl-Arylalanines
    标题:Phenylalanine Ammonia-Lyase: The Use Of Its Broad Substrate Specificity For Mechanistic Investigations And Biocatalysis-synthesis Ofl-Arylalanines
    摘要:Several Fluoro-And Chlorophenylalanines Were Found To Be Good Substrates Of Phenylalanine Ammonialyase (Pal/ec 4.3.1.5) From Parsley. The Enantiomerically Pure L-Amino Acids Were Obtained In Goad Yields By Reaction Of The Corresponding Cinnamic Acids With 5M Ammonia Solution (Buffered To Ph 10) In The Presence Of Pal. The Kinetic Constants For Nine Different Fluoro-And Chlorophenylalanines Do Not Provide A Rigorous Proof For But Are Consistent With The Previously Proposed Mechanism Comprising An Electrophilic Attack Of The Methylidene-Imidazolone Cofactor Of Pal At The Aromatic Nucleus As A First Chemical Step. In The Resulting Friedel-Crafts-Type Sigma Complex The Beta-Protons Are Activated For Abstraction And Consequently The Pro-S Is Abstracted By An Enzymic Base. Results From Semiempirical Calculations Combined With A Proposed Partial Active Site Model Showed A Correlation Between The Experimental Kinetic Constants And The Change In Polarization Of The Pro-S Cd-H Bond And Heat Of Formation Of The Ir Complexes,Thus Making The Electrophilic Attack At The Neutral Aromatic Ring Plausible. Furthermore,While 5-Pyrimidinylalanine Was Found To Be A Moderately Good Substrate Of Pal,2-Pyrimidinylalanine Was An Inhibitor.
    DOI:10.1002/1521-3765(20000915)6:18<3386::Aid-Chem3386>3.0.Co;2-5

    海关参考信息

    专利信息


    专利号:US-9206222-B2
    优先权日:2009-06-29
    标题:Solid phase peptide synthesis of peptide alcohols
    发明人:CAUSSIL-AMBLARD MURIEL; MARTINEZ JEAN; TAILHADES JULIEN
    权利人:CAUSSIL-AMBLARD MURIEL; MARTINEZ JEAN; TAILHADES JULIEN; CENTRE NAT RECH SCIENT
    摘要:The present invention relates to the synthesis of depsipeptides on solid phase support. Said depsipeptides are then implicated in a solution phase O—N acyl shift enabling to obtain the corresponding peptide alcohols.

    专利号:US-8546533-B2
    优先权日:2008-08-29
    标 题:Pipecolic linker and its use for chemistry on solid support
    发明人:MARTINEZ JEAN; ZAJDEL PAWEL; PAWLOWSKI MACIEJ; SUBRA GILLES
    权利人:MARTINEZ JEAN; ZAJDEL PAWEL; PAWLOWSKI MACIEJ; SUBRA GILLES; CENTRE NAT RECH SCIENT; UNIV MONTPELLIER 1; UNIV JAGELLONE; UNIV MONTPELLIER II
    摘要:The present invention relates to a pipecolic linker and its use as a solid-phase linker in organic synthesis. Said pipecolic solid-phase linker may be used for coupling functional groups chosen between primary amines, secondary amines, aromatic amines, alcohols, phenols and thiols. In particular, said pipecolic solid-phase linker may be used for peptide or pseudopeptide synthesis, such as the reverse N to C peptide synthesis or the retro-inverso peptide synthesis, or for the synthesis of small organic molecules.

    专利号:US-7763734-B2
    优先权日:2006-04-19
    标题 :Synthesis, structure and use of bisoxazolidines for asymmetric catalysis and synthesis
    发明人:WOLF CHRISTIAN; LIU SHUANGLONG
    权利人:UNIV GEORGETOWN
    摘要:One aspect of the invention relates to chiral bisoxazolidines and their use in asymmetric catalysis. The chiral bisoxazolidines are a novel class of compounds that is expected to find multiple applications, for example, in asymmetric synthesis. For example, a bisoxazolidine ligand enabled the catalytic enantioselective alkynylation and alkylation of a range of aromatic and aliphatic aldehydes, generating chiral propargylic alcohols and secondary alcohols in high yields and enantiomeric excess.

    专利号:WO-2011000848-A1
    优先权日:2009-06-29
    标题 :Solid phase peptide synthesis of peptide alcohols

    专利号:US-11759496-B2
    优先权日:2016-05-10
    标题:Compounds and pharmaceutical use thereof in the treatment of cancer
    发明人:SUSIN SANTOS A; KAROYAN PHILIPPE; MERLE-BERAL HÉLÈNE
    权利人:KAROYAN PHILIPPE
    摘要:The present invention relates to a compound or a pharmaceutical salt thereof comprising a hexapeptide sequence of formula (I), its method of synthesis and its use in anticancer therapy. The invention also relates to a pharmaceutical composition for use in the treatment of cancer comprising at least one soluble peptide according to the invention or at least one acid nucleic according to the invention or at least one expression vector according to the invention, or at least one host cell according to the invention and a pharmaceutically acceptable carrier.

    专利号:US-2012108748-A1
    优先权日:2009-06-29
    标 题:Solid phase peptide synthesis of peptide alcohols
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    主要参考文献

    [参考文献]: Fujita T, Et Al. Synthesis Of A Complete Set Of L-Difluorophenylalanines, L-(F2)Phe, As Molecular Explorers For The Ch/π Interaction Between Peptide Ligand And Receptor. Tetrahedron Letters. 2000, 41(6):923-927.

    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.
    摘要:Lloyd, C. M.; Dowell, K. F.; Brittain, W. D. G., Science of Synthesis: Modern Strategies in Organofluorine Chemistry, (2025) 2.
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