CAS: 86060-85-7; Fmoc-Gly-Opfp

该化合物是一种化学化合物,主要用于peptide合成中,作为氨酸甘油的保护组.该化合物具有氟乙基乙基(Fmoc)基(Fmoc)基)基组的特点,该组由于在基本条件下的稳定性和在温酸条件下易于去除,在固相合成中被广泛使用,是一个保护组.五氟联苯酯酯的存在增强了该化合物的再活性,使之适合组合反应.氟芳香环有助于该化合物独特的电子特性和水致癌性,可影响溶性并与其他分子的相互作用.氟辛基-Gly-Pfpp通常在惰性条件下处理,以防止降解,并且可溶解于有机溶剂,如二氯甲烷和二甲基化物的溶剂中.其应用范围超越了精密的合成,包括了精密的合成材料.

结构式图片

相似化合物

159631-29-5 125043-04-1 86060-86-8

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上下游产品

CAS号771-61-9 五氟苯酚 | CAS号29022-11-5 Fm°C-甘氨酸 | CAS号103321-49-9 N-(芴甲氧羰基)甘氨酰氯 | CAS号244633-31-6 4-硝基苯磺酸五氟苯酯 | CAS号88744-04-1 9-芴基甲基五氟苯基碳酸酯 | CAS号75539-79-6 Z-D-PHE-PHE-GLY-OH

合成工艺路线路线简述

  • 合成目标产物 Fmoc-Gly-Opfp 主要起始原料 9-Fluorenylmethyl Pentafluorophenyl Carbonate
  • 29022-11-5 + 771-61-9 = 86060-85-7
    反应条件:1.1 Reagents: Dicyclohexylcarbodiimide Solvents: Ethyl Acetate
    标题:9-Fluorenylmethyl Pentafluorophenyl Carbonate As A Useful Reagent For The Preparation Of N-[(9-Fluorenylmethoxy)Carbonyl] Amino Acids And Their Pentafluorophenyl Esters
    作者:Schon,Istvan; Kisfaludy,Lajos
    参考文献:Synthesis 日期:1986 卷标:(4) 页码:303-5]

    29022-11-5 + 771-61-9 = 86060-85-7
    反应条件:1.1 Reagents: 3,4-Dihydro-3-Hydroxy-4-Oxo-1,2,3-Benzotriazine
    标题:Synthesis Of Selenocysteine-Containing Cyclic Peptides Via Tandem N-To-S Acyl Migration And Intramolecular Selenocysteine-Mediated Native Chemical Ligation
    作者:Shimodaira,Shingo; Takei,Toshiki; Hojo,Hironobu; Iwaoka,Michio
    参考文献:Chemical Communications (Cambridge 日期:2018 卷标:54(83) 页码:11737-11740]

    29022-11-5 + 771-61-9 = 86060-85-7
    反应条件:1.1 Reagents: Thionyl Chloride Solvents: Dichloromethane1.2 Reagents: Pyridine Solvents: Tetrahydrofuran
    标题:A New Facile One-Pot Preparation Of Pentafluorophenyl And 3,4-Dihydro-4-Oxo-1,2,3-Benzotriazine-3-Yl Esters Of Fmoc Amino Acids
    作者:Jakobsen,Mogens Havsteen; Buchardt,Ole; Engdahl,Tom; Holm,Arne
    参考文献:Tetrahedron Letters 日期:1991 卷标:32(43) 页码:6199-202]

    103321-49-9 + 771-61-9 = 86060-85-7
    反应条件:1.1 Reagents: Sodium Bicarbonate Solvents: Dichloromethane,Water
    标题:Synthesis Of Pentafluorophenyl,2,4,5-Trichlorophenyl And Pentachlorophenyl Esters Of Fmoc-Amino Acids Using Fmoc-Amino Acid Chlorides As Intermediates
    作者:Babu,Vommina V. Suresh; Ananda,Kuppanna; Mathad,Raveendra I.
    参考文献:Letters In Peptide Science 日期:2001 卷标:7(4) 页码:239-242]

    29022-11-5 + 771-61-9 = 86060-85-7
    反应条件:1.1 Reagents: Dicyclohexylcarbodiimide Solvents: Ethyl Acetate; 2 H,0 °C
    标题:Pentafluorophenol
    作者:Jones,Keith; Deamicis,Carl
    参考文献:E-Eros Encyclopedia Of Reagents For Organic Synthesis 日期:2009 卷标:1 页码:1-9]

    29022-11-5 + 771-61-9 = 86060-85-7
    反应条件:1.1 Catalysts: Dicyclohexylcarbodiimide Solvents: Ethyl Acetate; 2 H,0 °C
    标题:Pentafluorophenol
    作者:Jones,Keith
    参考文献:E-Eros Encyclopedia Of Reagents For Organic Synthesis 日期:2001
📜Fmoc-甘氨酸置于吡啶,氯化亚砜体系中,用 四氢呋喃,二氯甲烷 作为反应溶剂,化学反应生成 N-芴甲氧羰基甘氨酸五氟苯酯
参考文献:一种新的简便的一锅制备fmoc氨基酸的五氟苯基(pfp)和3,4-二氢-4-氧代1,2,3-苯并三嗪-3-基(dhbt)酯.
标题:一种新的简便的一锅制备fmoc氨基酸的五氟苯基(pfp)和3,4-二氢-4-氧代1,2,3-苯并三嗪-3-基(dhbt)酯.
摘要:对于n五氟苯基和3,4-二氢-4-氧代-1,2,3-苯并三嗪-3-基酯的制备的新的一锅程序α-9-芴氨基酸不带有侧链保护基团是描述.该方法无需使用高度致敏的dcc,即可以高收率和纯度获得所需的活化酯.
DOI:10.1016/0040-4039(91)80788-8

海关参考信息

专利信息


专利号:US-6515039-B1
优先权日:1998-08-28
标 题:Method for the parallel and combinatory synthesis of compounds bound to a continuous polymeric solid phase supporting material
发明人:ULBRICHT MATHIAS; VOLKMER-ENGERT RUDOLF; GERMEROTH LOTHAR; WENSCHUH HOLGER
权利人:POLY AN GMBH
摘要:The invention relates to a method for the parallel and combinatory synthesis of compounds bound to a continuous polymeric solid phase supporting material. According to the method, a continuous polymeric solid phase supporting material is prepared, the material comprising a matrix of a supporting polymeric material and graft copolymer chains covalently bound to the supporting matrix, the graft copolymer chains having reactive groups being able to react with organic compounds, thereby forming spatially defined reaction sites. The method then comprises the sequential spotting of synthesis building blocks or reagents at the various reaction sites on the continuous solid phase supporting material to yield a substrate library of compounds bound to the solid phase supporting material, whereby each reaction site on the continuous solid phase supporting material determines the composition of the synthesized compound, which is bound directly on the supporting matrix via the reactive groups of the graft polymer chain.

专利号:US-2003138880-A1
优先权日:2001-08-24
标 题:Solid-phase synthesis of oligosaccharides and glycopeptides using glycosynthases
发明人:WITHERS STEPHEN G; JENSEN KNUD J; PETERSEN LARS; TOLBORG JAKOB L
权利人:UNIV BRITISH COLUMBIA
摘要:The present invention provides materials and methods for the solid-phase synthesis of oligosaccharides and glycopeptides. Such materials and methods include mutant glycosidase enzymes, or “glycosynthases,â€? chemically-derivatized acceptor molecules, and specific solid support matrices.

专利号:US-5126273-A
优先权日:1986-02-03
标题 :Monitoring method for the synthesis of a linear conbination of amino acid residues
发明人:SHEPPARD ROBERT; MELDAHL MORTEN
权利人:NOVOBIOCHEM AG
摘要:A monitoring method for application in solid phase peptide synthesis. In one aspect, the synthesis starts with an amino acid residue protected by an N-alpha-amino protecting group and involves the steps: (a) removing the N-alpha-amino protecting group to obtain an N-alpha-amino group, (b) adding an amino acid residue protected by an N-alpha-amino protecting group, via a peptide bond, to the N-alpha-amino group obtained in step (a) by use of a reactive protected amio acid derivative, and (c) repeating steps (a) and (b). The reaction system includes 3-hydroxy-1,2,3-benzotriazin-4(3H)-one or a derivative thereof; and the color of the reaction system or of a component thereof is monitored during the synthesis.

专利号:WO-8704713-A2
优先权日:1986-02-03
标题 :Monitoring method for the synthesis of a linear combination of amino acid residues

专利号:EP-0708751-A1
优先权日:1993-07-16
标题:Synthesis of combinatorial arrays of organic compounds through the use of multiple component combinatorial array syntheses

专利号:EP-0604552-A1
优先权日:1991-09-18
标 题 :PROCESS FOR THE SYNTHESIS OF VARIOUS COLLECTIONS OF OLIGOMERS.

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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):1793-1144.

合成参考文献


参考文献:10.1023/a:1014547324918
摘要:Huet E, Brassart B, Cauchard J, Debelle L, Birembaut P, Wallach J, Emonard H, Polette M, Hornebeck W. Cumulative influence of elastin peptides and plasminogen on matrix metalloproteinase activation and type I collagen invasion by HT-1080 fibrosarcoma cells. Clinical & Experimental Metastasis. 2002 Mar;19(2):107–17. doi: 10.1023/a:1014547324918.
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