CAS: 10172-89-1; N-Acetyl-D-Phenylalanine

该化合物是一种氨酸衍生物,其特点是含有附属于苯丙氨酸链氮的乙酰基体,该化合物是一种手性分子,以两种对称形式存在,其名称(-)表明其具体的立体化学特性,通常是一种白色至白晶状固体,在水和乙醇等极地溶剂中溶解,反映其极性,因为氨基和乙基功能组而具有极性,该化合物经常用于生物化学研究和药物应用,特别是蛋白合成和酶活动研究,因为其结构与天然氨基酸相似,其酶性会影响化合物的再活动及其与生物系统的互动,使其成为医药化学和药物设计的宝贵工具.此外,(-)-N-乙基苯基苯基氨可以展示具体的生物活动,尽管需要详细研究来说明其影响的全部范围.

结构式图片

相似化合物

2018-61-3 2901-75-9 2361-96-8

上下游产品

(R,S)-N-acetyl phenylalanine (1S)-endo-fenchylamine (1S,2S)-2-amino-1-(4-nitrophenyl)propane-1,3-diol D-(R)-phenylalanineD-(R)-phenylalanine (R)-ethyl N-acetylphenylalanine (2R,3R)-2-((R)-2-Acetylamino-3-phenyl-propionylamino)-3-hydroxy-butyric acid benzyl ester 4-(B°C-tyrosylamino)-1-(N-acetyl-D-phenylalanyl)piperidine

合成工艺路线路线简述

    D-苯丙氨酸置于sodium Hydroxide,乙酸酐体系中,用 水 用作溶剂,化学反应生成N-乙酰-D-苯丙氨酸
    参考文献:Optical Resolution Of Alkyl Esters Of Dl-Phenylalanine
    标题:Optical Resolution Of Alkyl Esters Of Dl-Phenylalanine
    摘要:用n-酰基-D-苯丙氨酸处理dl-苯丙氨酯,形成相应的l-苯丙氨酯和n-酰基-D-苯丙氨酸的不溶性盐.通过在dl-苯丙氨酯或l-苯丙氨酸的烷基酯的存在下重新结晶纯化盐.分离,纯化的盐被分解以获得所需的l-苯丙氨酯,这是制备人工甜味剂的重要原料.

    海关参考信息

    专利信息


    专利号:US-7317129-B2
    优先权日:2002-06-07
    标 题:Chemical synthesis of reagents for peptide coupling
    发明人:RAINES RONALD T; KIESSLING LAURA L; NILSSON BRADLEY L; HE YI; SOELLNER MATTHEW B; HINKLIN RONALD J
    权利人:WISCONSIN ALUMNI RES FOUND
    摘要:The present invention provides improved methods for synthesis of phosphinothiol reagents, as well as novel protected reagents, for use in formation of amide bonds, and particularly, for peptide ligation. The invention provides phosphine-borane complexes useful as reagents in the formation of amide bonds, particularly for the formation of an amide bond between any two of an amino acid, a peptide, or a protein.

    专利号:US-4985567-A
    优先权日:1988-03-07
    标题:Chiral phosphinopyrrolidine compounds and their use for asymmetric synthesis of optically active compounds
    发明人:ACHIWA KAZUO; TAKEDA HIDEO
    权利人:KAZUO ACHIWA; FUJI YAKUHIN KOGYO KK
    摘要:New chiral phosphinopyrrolidine compounds of the general formula: ##STR1## wherein R 1 is hydrogen or --COA 1 , --COOA 2 , --CONHA 3 , --SO 2 A 4 or --PO(A 5 ) 2 , A 1 , A 2 , A 3 , A 4 and A 5 each represents independently alkyl or aryl, R 2 is phenyl, di(lower-alkyl)aminophenyl, lower-alkoxyphenyl or 3,5-dimethyl-4-methoxyphenyl, and R 3 is phenyl, lower-alkylphenyl, di(lower-alkyl)aminophenyl, lower-alkoxyphenyl or 3,5-dimethyl-4-methoxyphenyl, with the proviso that R 2 and R 3 may not simultaneously by phenyl, p-di(lower-alkyl)-aminophenyl or p-lower-alkoxyphenyl, as well as the use of these compounds as ligand for a metal complex catalyst for asymmetric synthesis of optically active compounds. The new chiral phosphinopyrrolidine compounds are useful ligands which attain both of high optical yield and high reaction efficiency in catalytic asymmetric reduction.

    专利号:US-4891442-A
    优先权日:1987-03-09
    标 题 :Process for synthesis of β-phenylalanine
    发明人:LIN JIANG-JEN; KNIFTON JOHN F
    权利人:TEXACO INC
    摘要:N-acetyl-β-phenylalanine is synthesized by reacting phenylacetaldehyde, acetamide and synthesis gas with a catalyst comprising a cobalt-containing compound in conjunction with a cocatalyst that may be either a Group VB or VIB containing ligand, or a rhodium compound optionally bonded to one or more Group VB or VIB donor ligands, at a temperature of at least 50° C. and a pressure of at least 500 psi.

    专利号:US-6380416-B2
    优先权日:1997-06-13
    标题:Asymmetric synthesis catalyzed by transition metal complexes with rigid chiral ligands
    发明人:ZHANG XUMU
    权利人:PENN STATE RES FOUND
    摘要:This invention is to develop novel transition metal catalysts for the practical synthesis of important chiral molecules. The invention emphasizes asymmetric catalysis based on chiral bidentate phosphine ligands with cyclic ring structures which could be used to restrict conformational flexibility of the ligands and thus the efficiency of chiral transfer can be enhanced through the ligand rigidity.

    专利号:US-7230135-B2
    优先权日:2000-12-13
    标 题 :Synthesis of P-chiral bisphospholane ligands and their transition metal complexes for use as asymmetric hydrogenation catalysts
    发明人:HOGE II GARRETT STEWART; GOEL OM PRAKASH
    权利人:WARNER LAMBERT CO
    摘要:P-chiral bisphospholane ligands and methods for their preparation are described. Use of metal/P-chiral bisphospholane complexes to catalyze asymmetric transformation reactions to provide high enantiomeric excesses of formed compounds is also described.

    专利号:US-10947231-B2
    优先权日:2009-05-27
    标题:Processes for the preparation of substituted tetrahydro beta-carbolines
    发明人:HWANG PETER SEONGWOO; MOON YOUNG-CHOON; TAMIL ARASU; QI HONGYAN; ALMSTEAD NEIL
    权利人:PTC THERAPEUTICS INC
    摘要:Provided herein are improved processes for the synthesis of substituted tetrahydro beta-carboline derivatives. In particular, provided herein are improved processes useful for the preparation of (S)-4-chlorophenyl 6-chloro-1-(4-methoxyphenyl)-3,4-dihydro-1H-pyrido[3,4-b]indole-2(9H)-carboxylate. Formula (I):
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    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):1793-807.
    [参考文献]: J C Lacey, Et Al. Stereoselective Formation Of Bis(Alpha-Aminoacyl) Esters Of 5'-Amp Suggests A Primitive Peptide Synthesizing System With A Preference For L-Amino Acids. Biochim Biophys Acta. 1991 Feb 15;1076(3):395-400.
    [参考文献]: K Okajima, Et Al. Studies On The Mechanism For Renal Elimination Of N-Acetylphenylalanine: Its Pathophysiologic Significance In Phenylketonuria. J Lab Clin Med. 1985 Jan;105(1):132-8.
    [参考文献]: K Y Xu, Et Al. Acid Dissociation Constant And Apparent Nucleophilicity Of Lysine-501 Of The Alpha-Polypeptide Of Sodium And Potassium Ion Activated Adenosinetriphosphatase. Biochemistry. 1989 Aug 22;28(17):6894-9.
    [参考文献]: Magnus Stdeman, Et Al. Importance Of Product Inhibition In The Kinetics Of The Acylase Hydrolysis Reaction By Differential Stopped Flow Microcalorimetry. Anal Biochem. 2002 Sep 15;308(2):285-93.

    合成参考文献


    摘要:Joó, F., Science of Synthesis: Water in Organic Synthesis, (2012) 1, 107.
    摘要:Joó, F., Science of Synthesis: Water in Organic Synthesis, (2012) 1, 105.
    参考文献:10.1016/j.jmb.2004.07.023|10.2210/pdb1xpy/pdb|10.2210/pdb1xs2/pdb
    摘要:Wang WC, Chiu WC, Hsu SK, Wu CL, Chen CY, Liu JS, Hsu WH. Structural basis for catalytic racemization and substrate specificity of an N-acylamino acid racemase homologue from Deinococcus radiodurans. J Mol Biol. 2004 Sep 03;342(1):155–69. doi: 10.1016/j.jmb.2004.07.023.
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