CAS: 942518-20-9; (S)-2-((((9H-Fluoren-9-yl)Methoxy)Carbonyl)Amino)-4-Azidobutanoic Acid

该化合物是一种化学化合物,其独特的结构特征包括氟基化合物,甲基碳基化合物混合物和氮功能组;Azido组(-N3)的存在表明有反应的潜力,特别是在点击化学应用方面,使其在生物合成和材料科学方面有用;氟乙烯组有助于化合物的水利恐惧特性,从而影响其溶解性和与生物系统的互动;氨基酸柱表明,该化合物可能具有氨基酸的典型特性,例如有色性,而(S)的配置表明具体的立体化学特征会影响其生物活动和相互作用;该化合物还可能参与浸泡合成,或成为医药化学中更为复杂的分子的建筑块.

结构式图片

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942518-29-8 1097192-04-5 159610-89-6

物理性质

MSDS等安全信息

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N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (2S)-2-amino-4-azidobutanoic acid α-(9-fluorenylmethoxycarbonyl)-L-2,4-diaminobutyric acidNα-(9-fluorenylmethoxycarbonyl)-L-2,4-diaminobutyric acid 2-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-glutamineN2-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-glutamine Nα-Ac-Lys-Gly-hAla(γ-N3)-Ser-Ile-Gln-Nle(-yl)-Leu-Arg-NH2 Nα-Ac-Lys-Gly-Nle(-yl)-Ser-Ile-Gln-hAla(γ-N3)-Leu-Arg-NH2

合成工艺路线路线简述

  • 125238-99-5 = 942518-20-9
    反应条件:1.1 Reagents: Trifluoroacetic Acid Solvents: Dichloromethane; 2 H,Rt1.2 Reagents: Potassium Carbonate,Imidazole-1-Sulfonyl Azide Hydrochloride Catalysts: Copper Sulfate Solvents: Methanol,Dichloromethane,Water; Ph 9,Rt; Overnight,Rt
    标题:Total And Semisyntheses Of Polymyxin Analogs With 2-Thr Or 10-Thr Modifications To Decipher The Structure-Activity Relationship And Improve The Antibacterial Activity
    作者:Li,Jian; Guan,Dongliang; Chen,Feifei; Shi,Weiwei; Lan,Lefu; Et Al
    参考文献:Journal Of Medicinal Chemistry 日期:2021 卷标:64(9) 页码:5746-5765]

    28920-43-6 + 120042-08-2 = 942518-20-9
    反应条件:1.1 Reagents: Trifluoroacetic Acid Solvents: Dichloromethane; Rt1.2 Reagents: Sodium Carbonate Solvents: 1,4-Dioxane,Water; 0 °C1.3 4 H,Rt1.4 Reagents: Hydrochloric Acid Solvents: Water; Acidified,Rt
    标题:Expanding The Diversity Of Chemical Protein Modification Allows Post-Translational Mimicry
    作者:Van Kasteren,Sander I.; Kramer,Holger B.; Jensen,Henrik H.; Campbell,Sandra J.; Kirkpatrick,Joanna; Et Al
    参考文献:Nature (London 日期:2007 卷标:446(7139) 页码:1105-1109]

    71989-20-3 = 942518-20-9
    反应条件:1.1 Reagents: Iodobenzene Diacetate Solvents: Acetonitrile,Ethyl Acetate,Water; 1 H,Rt; Overnight,Rt; 4 H,Rt1.2 Reagents: Trifluoromethanesulfonic Anhydride,Sodium Azide Solvents: Dichloromethane,Water; 20 Min,0 °C; 15 Min,0 °C; 5 H,Rt1.3 Reagents: Sodium Bicarbonate Catalysts: Copper Sulfate Solvents: Methanol,Water; Overnight,Rt1.4 Reagents: Hydrochloric Acid Solvents: Water; Ph 2
    标题:Reagent-Based Diversity-Oriented Synthesis Of Triazolo[1,5-A][1,4]Diazepine Derivatives From Polymer-Supported Homoazidoalanine
    作者:Kralova,Petra; Soural,Miroslav
    参考文献:Journal Of Organic Chemistry 日期:2021 卷标:86(12) 页码:7963-7974]

    = 942518-20-9
    反应条件:1.1 Reagents: Potassium Carbonate,1H-Imidazole-1-Sulfonyl Azide,Sulfate (1:1) Catalysts: Copper Sulfate Solvents: Methanol,Water; 16 H,Ph 8 - 9,Rt
    标题:Triazolyl-Substituted Aminoamides As Buche Inhibitors And Their Preparation
    参考文献:Brazil]

    161420-87-7 = 942518-20-9 [标题:Reaction Conditions
    标题:Design,Synthesis,And Conformational Studies Of [dota]-Octreotide Analogs Containing [1,2,3]Triazolyl As A Disulfide Mimetic
    作者:Testa,Chiara; D'Addona,Debora; Scrima,Mario; Tedeschi,Anna Maria; D'Ursi,Anna Maria; Et Al
    参考文献:Peptide Science (Hoboken 日期:2018 卷标:110(5)]

    161420-87-7 = 942518-20-9 [标题:Reaction Conditions
    标题:1,4-Disubstituted-[1,2,3]Triazolyl-Containing Analogues Of Mt-Ii: Design,Synthesis,Conformational Analysis,And Biological Activity
    作者:Testa,Chiara; Scrima,Mario; Grimaldi,Manuela; D'Ursi,Anna M.; Dirain,Marvin L.; Et Al
    参考文献:Journal Of Medicinal Chemistry 日期:2014 卷标:57(22) 页码:9424-9434]

    161420-87-7 = 942518-20-9
    反应条件:1.1 Reagents: Sodium Bicarbonate,Trifluoromethanesulfonyl Azide Catalysts: Copper Sulfate Solvents: Methanol,Dichloromethane,Water; Rt; Overnight,Rt1.2 Reagents: Hydrochloric Acid Solvents: Water; Ph 1 - 2,Rt
    标题:Optimized Syntheses Of Fmoc Azido Amino Acids For The Preparation Of Azidopeptides
    作者:Picha,Jan; Budesinsky,Milos; Machackova,Katerina; Collinsova,Michaela; Jiracek,Jiri
    参考文献:Journal Of Peptide Science 日期:2017 卷标:23(3) 页码:202-214]

    942518-20-9 = 942518-20-9
    反应条件:1.1 Reagents: Diisopropylethylamine Solvents: Dichloromethane; 3 H,Rt1.2 Reagents: Diisopropylethylamine Solvents: Methanol,Dichloromethane; 6 Min,Rt
    标题:Water-Soluble Nhc-Cu Catalysts: Applications In Click Chemistry,Bioconjugation And Mechanistic Analysis
    作者:Diaz Velazquez,Heriberto; Ruiz Garcia,Yara; Vandichel,Matthias; Madder,Annemieke; Verpoort,Francis
    参考文献:Organic & Biomolecular Chemistry 日期:2014 卷标:12(46) 页码:9350-9356]

    161420-87-7 = 942518-20-9
    反应条件:1.1 Reagents: Potassium Carbonate,Trifluoromethanesulfonyl Azide Catalysts: Copper Sulfate Pentahydrate Solvents: Methanol,Water; Overnight,Ph 9.5,Rt1.2 Reagents: Hydrochloric Acid Solvents: Water; Ph 2
    标题:Maintaining Biological Activity By Using Triazoles As Disufide Bond Mimetics
    作者:Holland-Nell,Kai; Meldal,Morten
    参考文献:Angewandte Chemie 日期:2011 卷标:50(22) 页码:5204-5206]

    161420-87-7 = 942518-20-9
    反应条件:1.1 Reagents: Potassium Carbonate,Imidazole-1-Sulfonyl Azide Hydrochloride Catalysts: Copper Sulfate Solvents: Methanol,Dichloromethane,Water; 18 H,Ph 9,Rt
    标题:Efficient Synthesis Of Fmoc-Protected Azido Amino Acids
    作者:Lau,Yu Heng; Spring,David R.
    参考文献:Synlett 日期:2011 卷标:(13) 页码:1917-1919]

    71989-20-3 = 942518-20-9
    反应条件:1.1 Reagents: Bis(Trifluoroacetoxy)Iodobenzene Solvents: Dimethylformamide,Water; 15 Min,Rt1.2 Reagents: Pyridine; 14 H,Rt1.3 Reagents: Potassium Carbonate,1H-Imidazole-1-Sulfonyl Azide,Sulfate (1:1) Catalysts: Copper Sulfate Solvents: Methanol,Dichloromethane,Water; 18 H,Ph 9,Rt
    标题:Development Of Cell-Permeable,Non-Helical Constrained Peptides To Target A Key Protein-Protein Interaction In Ovarian Cancer
    作者:Wiedmann,Mareike M.; Tan,Yaw Sing; Wu,Yuteng; Aibara,Shintaro; Xu,Wenshu; Et Al
    参考文献:Angewandte Chemie 日期:2017 卷标:56(2) 页码:524-529]

    82911-69-1 + 359781-97-8 = 942518-20-9
    反应条件:1.1 Reagents: Trifluoroacetic Acid; 10 Min,Rt1.2 Reagents: Sodium Hydroxide Solvents: Water; 6 H,Rt1.3 Reagents: Hydrochloric Acid Solvents: Water; Ph 71.4 Reagents: Sodium Hydroxide Solvents: 1,4-Dioxane,Water; Ph 8,Rt; 3 H,Rt1.5 Reagents: Hydrochloric Acid Solvents: Water; Ph 3,Rt
    标题:Nα-Fmoc-Protected ω-Azido- And ω-Alkynyl-L-Amino Acids As Building Blocks For The Synthesis Of "Clickable" Peptides
    作者:Le Chevalier Isaad,Alexandra; Barbetti,Francesca; Rovero,Paolo; D'Ursi,Anna Maria; Chelli,Mario; Et Al
    参考文献:European Journal Of Organic Chemistry 日期:2008 卷标:(31) 页码:5308-5314
📜Nalpha-芴甲氧羰基-Nγ-羰-L-2,4-氨基丁酸置于1H-咪唑-1-磺酰叠氮盐酸盐,Copper(Ll) Sulfate Pentahydrate,Potassium Carbonate,三氟乙酸体系中,用 甲醇,二氯甲烷,水 作为反应溶剂,化学反应 2.0H,反应生成 (S)-2-(((9H-芴-9-基)甲氧基)羰基氨基)-4-叠氮丁酸
参考文献:总和半合成具有2 Thr或10 Thr修饰的多粘菌素类似物,以破解结构与活性之间的关系并提高抗菌活性
标题:总和半合成具有2 Thr或10 Thr修饰的多粘菌素类似物,以破解结构与活性之间的关系并提高抗菌活性
摘要:本文中,我们报道了一系列具有2-Thr和10-Thr修饰的多粘菌素类似物的全部和半合成,以揭示结构-活性关系(sar),此前尚未充分阐明.我们采用了两种全合成策略,分别促进了2-Thr或10-Thr的多样化替代.此外,使用半合成方法来实现2-Thr的选择性酯化或2-Thr和10-Thr的双重酯化.根据体外抗菌测定的结果,Sar分析表明,用带有疏水性侧链的氨基酸取代2-/ 10-Thr可以维持抗铜绿假单胞菌的活性但对其他经过测试的革兰氏阴性细菌有不同的影响.2-/ 10-Thr上的氨基乙酰基酯化具有优异的抗菌活性,化合物76对不同菌株的活性高2-8倍,对hk-2细胞系的毒性也较低.这项工作探讨了多粘菌素2-/ 10-Thr的sar,并为开发新型多粘菌素衍生物提供了有希望的策略.
DOI:10.1021/acs.Jmedchem.0C02217

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合成参考文献


参考文献:10.1055/s-0030-1260950
摘要:Spring D, Lau Y. Efficient Synthesis of Fmoc-Protected Azido Amino Acids. Synlett. 2011 Jul 14;2011(13):1917–9. doi: 10.1055/s-0030-1260950.
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