CAS: 95713-52-3; (S)-2-((5-Fluoro-2,4-Dinitrophenyl)Amino)Propanamide

该化合物是一种合成有机化合物,其独特的结构特征是含有与二硝基苯基苯协会联系在一起的衍生物,该化合物通常具有氨酸和芳香硝基硝基化合物的特性,例如极地溶剂中的溶性以及由于硝基苯基环上存在而具有的潜在反应性;二硝基苯基环上的二硝基苯替代物有助于其电子带回带特性,从而影响其再活动性和生物系统中的互动;此外,氟原子的存在可能会提高其脂性,并改变其相干特性;该化合物在各个领域都具有利益,包括医药化学和生物化学化学化合物,因为它在药物研制和生物化学探测中具有潜在用途;然而,应当遵循具体的安全和处理准则,因为与硝基化合物的化合物可能十分危险,可能需要在实验室环境中进行仔细管理.

结构式图片

欧盟法规

ECHA物质C&L通报

上下游产品

1,5-difluoro-2,4-dinitrobenzene (S)-alaninamide hydr°Chloride L-alanine amide D-alaninamide L-FDAA-L-Pro L-FDAA-D-leucine

合成工艺路线路线简述

  • 327-92-4 + 7324-05-2 = 95713-52-3
    反应条件:1.1 Reagents: Sodium Hydroxide,Sulfuric Acid Magnesium Salt (1:1) Solvents: Acetone,Water; 3 H,Rt1.2 Solvents: Acetone; Rt; 0.5 H,Rt
    标题:Direct Amidation Of Unprotected Amino Acids Using B(Och2Cf3)3
    作者:Lanigan,Rachel M.; Karaluka,Valerija; Sabatini,Marco T.; Starkov,Pavel; Badland,Matthew; Et Al
    参考文献:Chemical Communications (Cambridge 日期:2016 卷标:52(57) 页码:8846-8849]

    = 95713-52-3 [标题:Reaction Conditions
    标题:Preparation Of Novel Nα-(5-Fluoro-2,4-Dinitrophenyl)-N-(Aminoalkyl)Amino Acid Amide Derivatives As Optical Resolution Labeling Agents For Determination Of Absolute Configuration Of Amino Acids
    参考文献:Japan]

    327-92-4 + 33208-99-0 = 95713-52-3
    反应条件:1.1 Reagents: Sodium Bicarbonate Solvents: Acetone,Water; 1 H,40 °C
    标题:Indirect Resolution Of Enantiomers Of Certain Dl-Amino Acids By Liquid Chromatography Via Diastereomer Formation With Marfey'S Reagent And Its Leucine Variant
    作者:Bhushan,Ravi; Tanwar,Shivani
    参考文献:Proceedings Of The National Academy Of Sciences 日期:2009 卷标:79(3) 页码:241-251]

    327-92-4 + 33208-99-0 = 95713-52-3
    反应条件:1.1 Reagents: Sodium Bicarbonate Solvents: Acetone,Water; 1 H,40 °C
    标题:Synthesis And Application Of New Chiral Variants Of Marfey'S Reagent For Liquid Chromatographic Separation Of The Enantiomers Of α-Amino Acids
    作者:Bhushan,R.; Kumar,V.
    参考文献:Acta Chromatographica 日期:2008 卷标:20(3) 页码:329-347]

    327-92-4 + 7324-05-2 = 95713-52-3
    反应条件:1.1 Reagents: Sodium Hydroxide,Sulfuric Acid Magnesium Salt (1:1) Solvents: Acetone,Water; 3 H,Rt1.2 Solvents: Acetone; Rt; 0.5 H,Rt
    标题:B(Och2Cf3)3-Mediated Direct Amidation Of Pharmaceutically Relevant Building Blocks In Cyclopentyl Methyl Ether
    作者:Karaluka,Valerija; Lanigan,Rachel M.; Murray,Paul M.; Badland,Matthew; Sheppard,Tom D.
    参考文献:Organic & Biomolecular Chemistry 日期:2015 卷标:13(44) 页码:10888-10894]

    327-92-4 + 4726-84-5 = 95713-52-3
    反应条件:1.1 Reagents: Sodium Hydroxide,Sulfuric Acid Magnesium Salt (1:1) Solvents: Acetone,Water; 3 H,Rt1.2 Solvents: Acetone; Rt; 30 Min,Rt
    标题:Catalytic Modification Of Dehydroalanine In Peptides And Proteins By Palladium-Mediated Cross-Coupling
    作者:De Bruijn,A. Dowine; Roelfes,Gerard
    参考文献:Chemistry - A European Journal 日期:2018 卷标:24(48) 页码:12728-12733]

    = 95713-52-3 [标题:Reaction Conditions
    标题:A Nonempirical Method Using Lc/ms For Determination Of The Absolute Configuration Of Constituent Amino Acids In A Peptide: Elucidation Of Limitations Of Marfey'S Method And Of Its Separation Mechanism
    作者:Fujii,Kiyonaga; Ikai,Yoshitomo; Mayumi,Tsuyoshi; Oka,Hisao; Suzuki,Makoto; Et Al
    参考文献:Analytical Chemistry 日期:1997 卷标:69(16) 页码:3346-3352]

    = 95713-52-3 [标题:Reaction Conditions
    标题:Determination Of D-Amino Acids. Ii. Use Of A Bifunctional Reagent,1,5-Difluoro-2,4-Dinitrobenzene
    作者:Marfey,Peter
    参考文献:Carlsberg Research Communications 日期:1984 卷标:49(6) 页码:591-6
📜L-丙氨酰胺,1,5-二氟-2,4-二硝基苯置于magnesium Sulfate,Sodium Hydroxide体系中,用 水,丙酮 作为反应溶剂,化学反应 3.5H,以57%的收率获得产物n-A-(2,4-二硝基-5-氟苯基)-L-丙氨酸
参考文献:钯介导的交叉偶联催化多肽和蛋白质中脱氢丙氨酸的催化修饰
标题:钯介导的交叉偶联催化多肽和蛋白质中脱氢丙氨酸的催化修饰
摘要:脱氢丙氨酸(dha)是一种非常通用的非规范氨基酸,通常在抗菌肽中发现.本文中,我们介绍了通过钯介导的交叉偶联反应对dha的催化修饰.通过使用pd(edta)(oac)2作为水溶性催化剂,多种芳基硼酸与蛋白质和多肽(如乳链菌肽)中的脱水残基偶联.交叉偶联反应既产生了保留了α-碳的sp 2-杂化的heck产物,也产生了共轭加成产物.该反应可在温和的水性条件下进行,这使该方法成为生物正交催化方法的一个有吸引力的补充.
DOI:10.1002/chem.201802846

海关参考信息

专利信息


专利号:US-12421534-B2
优先权日:2021-11-10
标 题 :Engineered enzymes and method for the synthesis of diverse tyrosine analogs
发明人:ALMHJELL PATRICK J; ARNOLD FRANCES H
权利人:CALIFORNIA INST OF TECHN
摘要:Provided herein is an engineered tryptophan synthase β-subunit (TrpB) that catalyzes the synthesis of tyrosine, tyrosine analogs, or salts thereof. Also provided herein are methods for preparing tyrosine, tyrosine analogs, or a salt thereof using the engineered TrpB described herein.

专利号:WO-9707129-A1
优先权日:1995-08-18
标题 :Solution synthesis of peripheral acting analgesic opioid tetrapeptides
发明人:RINALDI NICHOLAS
权利人:IAF BIOCHEM INT; RINALDI NICHOLAS
摘要:This invention provides a bulk scale process for the solution synthesis of enantiomerically pure peripherally acting analgesic opioid tetrapeptides corresponding to formula (I): Tyr-(D)R1-R2-R3-NH2, where R1 is Ala or Arg; R2 is Phe or Phe(p-F); and R3 is Phe or Phe(p-F). A new and unique multi-step process is disclosed comprising the joining of two dipeptides using standard solution phase synthesis techniques, but adjusting the individual factors (e.g., solvents, activating agents, neutralizing agents etc.), to minimize racemization of the second amino acid. Tremendous cost efficiencies are achieved due to elimination of traditional sequential blocking-deblocking cycles and multiple chromatographic purification steps, which also enables these simple kilogram quantity methods to be scaled up to commercial production.

专利号:WO-2012059797-A1
优先权日:2010-11-04
标题 :Process for synthesis of (s) - pregabalin
发明人:ROY BHAIRAB NATH; SINGH GIRIJ PAL; LATHI PIYUSH SURESH; AGRAWAL MANOJ KUNJABIHARI; MITRA RANGAN; RUPNAWAR MANOJ DATTATRAYA
权利人:LUPIN LTD; ROY BHAIRAB NATH; SINGH GIRIJ PAL; LATHI PIYUSH SURESH; AGRAWAL MANOJ KUNJABIHARI; MITRA RANGAN; RUPNAWAR MANOJ DATTATRAYA
摘要:Improved process for the synthesis of (S)-pregabalin having more than 99% ee through (S) 3-cyano-5-methyl-hexanoic acid has been developed. In addition to above, a novel process for resolution of ( RS ) - 3-cyano-5-methyl-hexanoic acid through diastereomeric salt formation with cinchonidine to obtain ( S ) - 3-cyano-5-methyl-hexanoic acid in high yield and high optical purity has been developed and furthermore process for recovery/ reuse of cinchonidine is also developed to improve the overall process efficiency.

专利号:US-5280093-A
优先权日:1989-06-29
标题 :Chiral polymers for the synthesis of pure enantiomers of amino acids
发明人:JACQUIER ROBERT; CALMES MONIQUE; DAUNIS JACQUES
权利人:RHONE POULENC CHIMIE
摘要:The present invention relates to chiral polymers and to their uses for operations of asymmetric synthesis, deracemization and optical inversion. n These polymers are characterized in that they comprise: n a chiral unit n a functionalizing unit n an optional crosslinking unit n Application to chiral organic synthesis.

专利号:US-2022372533-A1
优先权日:2017-06-30
标 题 :Transgenic microorganisms and synthesis of piperazic acid, piperazic acid containing products, and derivatives thereof
发明人:VAN DYKE-BLODGETT JOSHUA; HU YIFEI
权利人:VAN DYKE BLODGETT JOSHUA; HU YIFEI; WASHINGTON UNIVERSITY ST LOUIS
摘要:Among the various aspects of the present disclosure is the provision of a biological and biochemical production of piperazic acid derived from the newly discovered production pathway for L-piperazic acid. One aspect of the present disclosure includes a transgenic microorganism (e.g., bacteria) engineered to accumulate piperazic acid and derivatives thereof, including a piperazic acid (Piz)-containing product. Another aspect of the present disclosure includes biochemical and biological methods for producing piperazic acid and derivatives thereof, including a piperazic acid (Piz)-containing product. Another aspect of the present disclosure includes compositions and methods of using isotopically labeled piperazic acid and derivatives thereof, including a piperazic acid (Piz)-containing product.

专利号:US-2025034607-A1
优先权日:2021-12-03
标题 :Process of Synthesizing (R)-3-aminobutan-1-ol
发明人:BOBKO MARK; FUERST DOUGLAS; MORGAN CHRISTOPHER
权利人:VIIV HEALTHCARE CO
摘要:The present invention relates to an aminotransaminase useful in the synthesis of (R)-3-aminobutan-1-ol (RABO). The present invention also provides a process of preparing (R)-3-aminobutan-1-ol (RABO) with the disclosed aminotransaminase.

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品牌试剂参考报价(招募中)

📌 第三方产品分析报告

✅ COA系统入驻 | 共享模式

主要参考文献

[参考文献]: B S Foster, Et Al. Enantiomeric Determination Of Amphetamine And Methamphetamine In Urine By Precolumn Derivatization With Marfey'S Reagent And Hplc. J Anal Toxicol. 1998 Jul-Aug;22(4):265-9.
[参考文献]: E Harth-Fritschy, Et Al. Esterification Of 9-Fluorenylmethoxycarbonyl-Glycosylated Serine And Cysteine Derivatives With An Hydroxymethyl Resin. J Pept Res. 1997 Dec;50(6):415-20.
[参考文献]: En Huang, Et Al. Biosynthesis Of The New Broad-Spectrum Lipopeptide Antibiotic Paenibacterin In Paenibacillus Thiaminolyticus Osy-Se. Res Microbiol. 2014 Apr;165(3):243-51.
[参考文献]: Eric J Dimise, Et Al. Structure Elucidation And Biosynthesis Of Fuscachelins, Peptide Siderophores From The Moderate Thermophile Thermobifida Fusca. Proc Natl Acad Sci U S A. 2008 Oct 7;105(40):15311-6.
[参考文献]: Michael J Berna, Et Al. Quantification Of Serine Enantiomers In Rat Brain Microdialysate Using Marfey'S Reagent And Lc/ms/ms. J Chromatogr B Analyt Technol Biomed Life Sci. 2007 Feb 1;846(1-2):359-63.

合成参考文献


参考文献:10.1016/s0021-9673(98)01081-4
摘要:Török G, Péter A, Gaucher A, Wakselman M, Mazaleyrat JP, Armstrong DW. High-performance liquid chromatographic separation of novel atropic alpha,alpha-disubstituted-beta-amino acids, either on different beta-cyclodextrin-bonded phases or as their 1-fluoro-2,4-dinitrophenyl-5-L-alanine amide derivatives. J Chromatogr A. 1999 Jun 18;846(1-2):83–91. doi: 10.1016/s0021-9673(98)01081-4.
参考文献:10.1002/bmc.1013
摘要:Bhushan R, Kumar V. Indirect resolution of baclofen enantiomers from pharmaceutical dosage form by reversed-phase liquid chromatography after derivatization with Marfey's reagent and its structural variants. Biomed Chromatogr. 2008 Aug;22(8):906–11. doi: 10.1002/bmc.1013.
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