CAS: 86060-92-6; Fmoc-Phe-Opfp

该化合物是一种化学化合物,其结构复杂,包括一个全氟基化合物组和一个与氨酸L-苯丙氨相关的氟氧基碳基(Fmoc)保护组.该化合物通常用于peptide合成,特别是在固相双聚合成(SPPS)方面,因为氟化物组是氨基组的保护性协会,允许有选择的反应.五氟化物组的存在加强了该化合物在有机溶剂中的再活性和溶性,使之适合各种合成应用.此外,氟芳香环有助于该化合物独特的电子特性,从而影响其在生物系统中的互动.

结构式图片

相似化合物

86060-85-7 159505-85-8 86060-93-7

欧盟法规

ECHA物质C&L通报

上下游产品

CAS号771-61-9 五氟苯酚 | CAS号103321-57-9 N-(9-芴甲氧羰基)苯丙氨酰氯 | CAS号35661-40-6 Fm°C-L-苯丙氨酸 | CAS号244633-31-6 4-硝基苯磺酸五氟苯酯 | CAS号14533-84-7 三氟乙酸五氟苯酯 | CAS号96157-57-2 2,3,4,5,6-penta... | CAS号63-91-2 L-苯丙氨酸 | CAS号88744-04-1 9-芴基甲基五氟苯基碳酸酯 | CAS号5241-58-7 L-苯丙酰胺 | CAS号137593-52-3 GR 64349 | CAS号169624-67-3 N-芴甲氧羰基-苯丙氨酰-甘氨酸 | CAS号75539-79-6 Z-D-PHE-PHE-GLY-OH | CAS号5241-71-4 H-Asp-Phe-NH2

合成工艺路线路线简述

  • 771-61-9 + 35661-40-6 = 86060-92-6
    反应条件:1.1 Reagents: 4-Methylmorpholine,9-Fluorenylmethyl Chloroformate; 10 Min,-15 °C1.2 Solvents: Tetrahydrofuran; -15 °C -> Rt
    标题:9-Fluorenylmethyl Chloroformate (Fmoc-Cl) As A Useful Reagent For The Synthesis Of Pentafluorophenyl,2,4,5-Trichlorophenyl,Pentachlorophenyl,P-Nitrophenyl,O-Nitrophenyl And Succinimidyl Esters Of Nα-Urethane Protected Amino Acids
    作者:Tantry,Subramanyam J.; Babu,Vommina V. Suresh
    参考文献:Letters In Peptide Science 日期:2004 卷标:10(5-6) 页码:655-662]

    14533-84-7 + 35661-40-6 = 86060-92-6 [标题:Reaction Conditions
    标题:Preparation Of Pentafluorophenyl Esters Of Fmoc Protected Amino Acids With Pentafluorophenyl Trifluoroacetate
    作者:Green,Michael; Berman,Judd
    参考文献:Tetrahedron Letters 日期:1990 卷标:31(41) 页码:5851-2]

    26346-84-9 + 35661-40-6 = 86060-92-6
    反应条件:1.1 Reagents: Pyridine
    标题:Bis(Pentafluorophenyl) Sulfite As A New Reagent For The Preparation Of Pentafluorophenyl (Activated) Esters Of N-Protected Amino Acids
    作者:Il'Ina,A. V.; Davidovich,Yu. A.; Rogoshin,S. V.
    参考文献:Izvestiya Akademii Nauk Sssr 日期:1988 卷标:(12) 页码:2816-18]

    771-61-9 + 35661-40-6 = 86060-92-6
    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]

    771-61-9 + 35661-40-6 = 86060-92-6
    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
📜9-芴甲基五氟苯基碳酸酯置于碳酸氢钠,N,N'-二环己基碳二亚胺体系中,用 水,乙酸乙酯,丙酮 作为反应溶剂,化学反应 2.0H,反应生成 N-芴甲氧羰基-L-苯丙氨酸五氟苯酯
参考文献:Schoen,Istvan; Kisfaludy,Lajos,Synthesis,1986,# 4,P. 303-305
标题:Schoen,Istvan; Kisfaludy,Lajos,Synthesis,1986,# 4,P. 303-305

海关参考信息

专利信息


专利号:US-5545568-A
优先权日:1992-09-14
标题:Solid phase and combinatorial synthesis of compounds on a solid support
发明人:ELLMAN JONATHAN A
权利人:UNIV CALIFORNIA
摘要:Methods, compositions, and devices for synthesizing combinatorial libraries of various useful compounds, such as benzodiazepines, prostaglandins, β-turn mimetics and glycerol-derived drugs is described. In order to expediently synthesize such combinatorial libraries of derivatives based upon these core structures, a general methodology for the solid phase synthesis of these derivatives is also provided. This disclosure thus also describes an important extension of solid phase synthesis methods to nonpolymeric organic compounds.

专利号:US-7781488-B2
优先权日:2002-06-10
标 题:Post-cleavage sulfur deprotection for convergent protein synthesis by chemical ligation
发明人:BOTTI PAOLO; VILLAIN MATTEO; MANGANIELLO SONIA; GAERTNER HUBERT
权利人:AMYLIN PHARMACEUTICALS INC
摘要:The present invention provides a method and compositions for synthesizing an oligopeptide or polypeptide by convergent assembly of a plurality of pairs of oligopeptides in chemical ligation reactions. An important aspect of the present invention is an oligopeptide having a C-terminal disulfide-protected carboxythioester group that can be deprotected to spontaneously generate a free C-terminal thioester moiety. This allows a single precursor to participate in a succession of chemical ligation reactions, thereby making the convergent synthesis approach possible. The present invention is useful in methods for chemical synthesis of oligopeptides, polypeptides and proteins, and improves the efficiency of native chemical ligation reactions, particularly where four or more peptide fragments are used to assemble an oligopeptide, polypeptide or protein product.

专利号:US-5262331-A
优先权日:1989-08-28
标 题 :Method for monitoring in peptide synthesis
发明人:SALISBURY STEPHEN; TREMEER JOHN; OWEN DAVID; DAVIES JOHN
权利人:SALISBURY STEPHEN; TREMEER JOHN; OWEN DAVID; DAVIES JOHN
摘要:A method for monitoring the reaction between an activated carboxylic acid derivative and an amine, such as the formation of a peptide bond in peptide synthesis, whereby an inert anionic dye component and an inert cationic component are included in the reaction system, in small relative amounts compared to the carboxylic acid derivative. The distribution of the dye component to the cationic component, when separated from the amine component, is monitored and at a given maximum value indicates a substantially quantitative reaction.

专利号:US-5286789-A
优先权日:1989-05-26
标题:Solid phase multiple peptide synthesis
发明人:OKRONGLY DAVID; CLARK BRIAN R; SPESARD JACK
权利人:APPLIED IMMUNESCIENCES
摘要:Methods and compositions are provided, where oligopeptides are produced on a transparent surface while retaining transparency by the cyclical addition of protected monomers. Reagents are specifically selected to allow for efficient reproducible addition, while maintaining transparency of the support. Linkers are provided which permit retention of the oligopeptide to the surface or release of the oligopeptide at completion of the preparation of the oligopeptide. The oligopeptide bound to the support finds use in diagnostic assays, as well as other application, while the free oligopeptides may be used in a variety of ways.

专利号:EP-0400920-B1
优先权日:1989-05-26
标 题 :Solid phase multiple peptide synthesis
发明人:OKRONGLY DAVID; CLARK BRIAN R; SPESARD JACK
权利人:APPLIED IMMUNESCIENCES
摘要:Methods and compositions are provided, where oligopeptides are produced on a transparent surface while retaining transparency by the cyclical addition of protected monomers. Reagents are specifically selected to allow for efficient reproducible addition, while maintaining transparency of the support. Linkers are provided which permit retention of the oligopeptide to the surface or release of the oligopeptide at completion of the preparation of the oligopeptide. The oligopeptide bound to the support finds use in diagnostic assays, as well as other application, while the free oligopeptides may be used in a variety of ways.

专利号:EP-0450715-B1
优先权日:1990-04-02
标题 :Immunogenic compounds, the process for their synthesis and their use in the preparation of antimalaria vaccines
发明人:PESSI ANTONELLO; BIANCHI ELISABETTA; CORRADIN GIAMPIETRO
权利人:ENIRICERCHE SPA
摘要:A class of immunogenic compounds is described, definable by the formula (I): where: D is L-lysine or branched poly(L-lysine) with a number n of L-lysine amino acid residues (Lys) of a and epsilon amide linkage; n is a whole odd number varying from 1 to 15; A and B, which can be the same or different, are a polypeptide consisting of one or more plasmodial B epitopes covalently bound to one or more peptides with an amino acid sequence corresponding to that of a T epitope such as FNNFTVSFWLRVPKVSASHLEA (TT3) and QYIKANSKFIGITE (TT2), a compound of adjuvant activity, or A-CO or B-CO represent a direct bond or R-A-CO or R-B-CO are a protecting group for the alpha or epsilon -amino group of the L-lysine amino acid residue, with the condition that A and B are not both simultaneously an adjuvant or a direct bond or a protecting group; X is an amino acid residue in which R1 is the side chain of a amino acid residue chosen from L-Asp, L-His, L-Cys, L-Gln, L-Thr, L-Ala, L-Leu, L-Met, L-Phe, L-Glu, L-Arg, L-Tyr, L-Asn, L-Ser, L-Gly, L-Val, L-Ileu, L-Pro and L-Trp, and R2 is OH or NH2; R is hydrogen or an acyl radical; and the corresponding pharmaceutically acceptable salts of acid or basic addition. Compounds of formula (I) are particularly suitable as immunogens for preparing genetically non-restricted antimalaria vaccines, and in diagnostics for determining anti-Plasmodium antibodies in blood, serum and blood spot samples.

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品牌试剂参考报价(招募中)

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✅ COA系统入驻 | 共享模式

主要参考文献

[参考文献]: Rebecca M Turk-Macleod, Et Al. The Plausibility Of Rna-Templated Peptides: Simultaneous Rna Affinity For Adjacent Peptide Side Chains. J Mol Evol. 2012 Apr;74(3-4):217-25.

合成参考文献


参考文献:10.1055/s-0041-1737580
摘要:Synthesis of Versatile N-Protected Amino Acid Esters from Aryl 4-Nitrosulfonates. Synfacts. 2022 May 17;18(06):0699. doi: 10.1055/s-0041-1737580.
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