CAS: 51-65-0; 2-Amino-3-(4-Fluorophenyl)Propanoic Acid

该化合物是一种含氟芳烃氨基酸衍生物,可应用于制药和生化研究,其结构结构中含有一种氟替代苯环,增强了其作为peptide合成和药物开发的一个构件的效用.氟酸会影响电子和...

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合成工艺路线路线简述

    对氟肉桂酸置于phenylalanine Ammonia Lyase From Anabaena Variabilis,氨基甲酸铵体系中,化学反应 22.0H,以96%的收率获得产物dl-对氟苯丙氨酸
    参考文献:肉桂酸双酶法转化为2-芳基乙胺
    标题:肉桂酸双酶法转化为2-芳基乙胺
    摘要:羧酸(例如丙烯酸)向胺的转化是在合成有机化学中仍然具有挑战性的转化.尽管在自然代谢途径中普遍存在相似的部分,但出于这一目的,生物催化途径似乎已被忽略.本文中,我们介绍了一种双酶体系的概念和优化方法,它允许从容易获得的环取代肉桂酸合成β-苯乙胺衍生物.在通过两步方法表征了反应的两个部分之后,优化了允许单罐生物转化的一组条件.可逆的脱氨酶和不可逆的脱羧酶的组合,对串联的氨基酸中间体均具有特异性,
    DOI:10.1002/cctc.201902128

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    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-7122628-B2
    优先权日:2000-12-22
    标 题:Process for the synthesis of a peptide having a Trp residue
    发明人:JACKSON STEVEN ALLEN
    权利人:IPSEN MFG IRELAND LTD
    摘要:A process for the solid phase synthesis of a peptide having at least one thyptophan residue, wherein said method comprises temporarily protecting the indole ring of said tryptophan residue with a side chain protecting group which is labile to a base wherein said protecting group is removed during cleavage of said peptide from the solid support.

    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-6117974-A
    优先权日:1991-10-02
    标题:Libraries of backbone-cyclized peptidomimetics
    发明人:GILON CHAIM; HORNIK VERED
    权利人:PEPTOR LTD; YISSUM RES DEV CO
    摘要:Libraries of novel backbone-cyclized peptide analogs are formed by means of bridging groups attached via the alpha nitrogens of amino acid derivatives to provide novel non-peptidic linkages. Novel building units used in the synthesis of these backbone-cyclized peptide analogs are N(((-functionalized) amino acids constructed to include a spacer and a terminal functional group. One or more of these N(((-functionalized) amino acids are incorporated into a library of peptide sequences, preferably during solid phase peptide synthesis. The reactive terminal functional groups are protected by specific protecting groups that can be selectively removed to effect either backbone-to-backbone or backbone-to-side chain cyclizations. The invention is exemplified by libraries of backbone-cyclized bradykinin analogs, somatostatin analogs, BPI analogs and Substance P analogs having biological activity. Further embodiments of the invention are Interleukin-6 receptor derived peptides having ring structures involving backbone cyclization.

    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


    1: Gonti S, Westler WM, Miyagi M, Bann JG. Site-Specific Labeling and 19F NMR Provide Direct Evidence for Dynamic Behavior of the Anthrax Toxin Pore ϕ-Clamp Structure. Biochemistry. 2021 Jan 11. doi: 10.1021/acs.biochem.0c00833. Epub ahead of print. 7(7):bio036103. doi: 10.1242/bio.036103.
    3: Onselen RV, Downing S, Kemp G, Downing T. Investigating β-N-Methylamino-l- alanine Misincorporation in Human Cell Cultures: A Comparative Study with Known Amino Acid Analogues. Toxins (Basel). 2017 Dec 14;9(12):400. doi: 10.3390/toxins9120400.
    4: Hou Y, Hu W, Li X, Skinner JJ, Liu D, Wüthrich K. Solvent-accessibility of discrete residue positions in the polypeptide hormone glucagon by 19F-NMR observation of 4-fluorophenylalanine. J Biomol NMR. 2017 May;68(1):1-6. doi: 10.1007/s10858-017-0107-8. Epub 2017 May 15.

    合成参考文献


    摘要:Parmeggiani, F.; Galman, J. L.; Montgomery, S. L.; Turner, N. J., Science of Synthesis, (2019) , 408.
    摘要:Journal of Pharmacology and Experimental Therapeutics., 155(135), 1967 []
    摘要:
    参考文献:10.1093/oxfordjournals.jbchem.a022419
    摘要:Fujita T, Nose T, Nakajima M, Inoue Y, Costa T, Shimohigashi Y. Design and Synthesis of para-Fluorophenylalanine Amide Derivatives as Thrombin Receptor Antagonists. Journal of Biochemistry. 1999 Jul 01;126(1):174–9. doi: 10.1093/oxfordjournals.jbchem.a022419.
    参考文献:10.1007/s00259-001-0716-y|10.1007/s00259-002-0856-8
    摘要:Laverman P, Boerman OC, Corstens FH, Oyen WJ. Fluorinated amino acids for tumour imaging with positron emission tomography. European Journal of Nuclear Medicine and Molecular Imaging. 2002 Jan 11;29(5):681–90. doi: 10.1007/s00259-001-0716-y.
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