CAS: 33305-77-0; (S)-2-((Tert-Butoxycarbonyl)Amino)-3-(4-Nitrophenyl)Propanoic Acid

该化合物是一种氨基酸衍生物,其特点是氨基组中存在一种三丁氧碳基(Boc)保护组,而硝基组在苯环的副位置上存在一种.这种化合物通常用于浸泡合成,作为一种氨基酸L-苯麻拉尼的保护形式,允许有选择的反应,而不会干扰氨基组. Boc组在基本条件下保持稳定,但在酸性条件下很容易去除,因此在有机合成中是一种有价值的工具.硝基组有助于化合物的极性,并能够影响其在不同溶剂中的再活动性和溶性.此外,苯基环的存在具有芳香特性,可能影响化合物在生物系统中的相互作用.

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合成工艺路线路线简述

  • 合成目标产物 Boc-L-4-Nitrophe 主要起始原料 Di-Tert-Butyl Dicarbonate And 4-Nitro-3-Phenyl-L-Alanine
  • (文献来源)合成步骤主要原料 Di-Tert-Butyl Dicarbonate 和 4-Nitro-3-Phenyl-L-Alanine
甲基n-{[(2-甲基-2-丙基)氧基]羰基}-4-硝基苯丙氨酸酯置于lithium Hydroxide体系中,用 四氢呋喃,水 作为反应溶剂,化学反应生成 Boc-L-4-硝基苯丙氨酸
参考文献:Design,Synthesis And In Vitro Pharmacology Of Gluk1 And Gluk3 Antagonists. Studies Towards The Design Of Subtype-Selective Antagonists Through 2-Carboxyethyl-Phenylalanines With Substituents Interacting With Non-Conserved Residues In The Gluk Binding Sites
标题:Design,Synthesis And In Vitro Pharmacology Of Gluk1 And Gluk3 Antagonists. Studies Towards The Design Of Subtype-Selective Antagonists Through 2-Carboxyethyl-Phenylalanines With Substituents Interacting With Non-Conserved Residues In The Gluk Binding Sites
摘要:In Order To Identify Compounds Selective For The Gluk1 And Gluk3 Subtypes Of Kainate Receptors We Have Designed And Synthesized A Series Of (S)-2-Amino-3-((2-Carboxyethyl)Phenyl)Propanoic Acid Analogs With Hydrogen Bond Donating And Accepting Substituents On The Aromatic Ring. Based On Crystal Structures Of Gluk1 In Complex With Related Ligands,The Compounds Were Designed To Explore Possible Interactions With Non-Conserved Residues Outside The Glutamate Ligand Binding Site And Challenge The Water Binding Network. Apart From Obtaining Gluk1 Selective Antagonists One Analog With A Phenyl-Substituted Urea (Compound 31) Showed Some Preference For Gluk3 Over Gluk1-Receptors. Docking Studies Indicate That This Preference May Be Attributed To Contacts Between The Nh Of The Urea Substituent And Non-Conserved Ser741 And Ser761 Residues.
DOI:10.1016/j.Bmc.2014.07.045

海关参考信息

专利信息


专利号:US-7928236-B2
优先权日:2005-06-10
标题 :Fluorescent amino acid derivatives
发明人:TAKI MASUMI; SISIDO MASAHIKO
权利人:UNIV OKAYAMA NAT UNIV CORP
摘要:The subject of the present invention is to provide a fluorescent substance excitable under visible light, having higher photostability and a long fluorescence lifetime. Another subject is to provide a fluorescent substance consists of a non-natural amino acid applicable to peptide synthesis systems. n Searching fluorescent substances, which are fluorescent amino acids and excitable under visible light, having the lowest possible molecular weight for a high photostability resulted in forming a condensed polycyclic aromatic compound by subjecting a compound having an acridone structure to substitution with an amino acid and further condensation with a benzene ring. Thus, the subject is achieved by the fluorescent substance consisting of amino acid-substituted benzoacridone derivative excitable under visible light.
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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):1793-900.

合成参考文献


参考文献:10.1023/a:1020629501426
摘要:Bhargava KK, Zhang ZY, Palestro CJ, Acharya SA. Synthesis of aminobenzyltriethylenetetraaminohexaacetic acid: conjugation of the chelator to protein by an alkylamine linkage. J Protein Chem. 1999 Oct;18(7):761–70. doi: 10.1023/a:1020629501426.
参考文献:10.1007/s10337-024-04311-5
摘要:Zeng H, Peng J, Peng H, Wang X, Zhang Z, Yang H, Yu J, Wu J. Preparation of Polymer-Based Amino Acid Stationary Phase and Its Application for Mixed-Mode Chromatography. Chromatographia. 2024 Feb 06;87(3):147–57. doi: 10.1007/s10337-024-04311-5.
参考文献:10.1134/s1068162024050297
摘要:Azev VN, Mustaeva LG, Gorbunova EY, Baidakova LK, Chulin AN, Maslov LN, Mukhomedzyanov AV, Molchanov МВ, Miroshnikov AI. Boc/Bzl Solid-Phase Synthesis of Deltorphin II and Its Analogs without the Utilization of Anhydrous Hydrogen Fluoride. Russ J Bioorg Chem. 2024 Oct;50(5):1701–9. doi: 10.1134/s1068162024050297.
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