CAS: 13726-76-6; (S)-2-((Tert-Butoxycarbonyl)Amino)-5-Guanidinopentanoic Acid

该化合物是氨酸亚氨酸亚氨酸的衍生物,其特点是存在一种乙型丁氧基碳酸(Boc)保护组,该化合物通常用于peptide合成,特别是形成含有硅酸的,因为Boc组在混合反应中保护氨基组;Boc-Arg的结构包括一个组,该组是的特征,有助于其基本性和形成氢结的能力;Boc组的存在加强了酸性条件下氨酸的稳定性,使其在合成程序期间更容易处理;Boc-Arg通常在有机溶剂(如二氯甲烷和二甲基基胺)中可溶解,但水中的溶解性有限;这种化合物在生物化学和制药研究中至关重要,特别是在基于丙基药物的研制过程中,以及在涉及蛋白质相互作用的研究中具有关键性.

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合成工艺路线路线简述

    📜(S)-2-Tert-Butoxycarbonylamino-5-Guanidino-Pentanoic Acid Tert-Butyl Ester置于cerium(III) Chloride,Sodium Iodide体系中,用 乙腈 用作溶剂,化学反应 2.0H,以79%的收率获得n-Boc-L-精氨酸
    参考文献:Selective Deprotection Of N-Boc-Protected Tert-Butyl Ester Amino Acids By The Cecl3.7H2O−nai System In Acetonitrile
    标题:Selective Deprotection Of N-Boc-Protected Tert-Butyl Ester Amino Acids By The Cecl3.7H2O−nai System In Acetonitrile
    摘要:
    Doi:10.1021/jo010010Y

    海关参考信息

    专利信息


    专利号:US-6376649-B1
    优先权日:1998-12-18
    标题 :Methods for the synthesis of α- hydroxy-β-amino acid and amide derivatives
    发明人:SEMPLE JOSEPH E; LEVY ODILE E
    权利人:CORVAS INT INC
    摘要:Methods for the synthesis of alpha-hydroxy-beta-amino acid and amide derivatives and alpha-ketoamide derivatives and novel derivatives made by these methods are provided. These methods involve reacting a N-terminally blocked (protected) aminoaldehyde with an isonitrile and a carboxylic acid to give an amino-alpha-acyloxy carboxamide. The acyloxy group may be removed to give the derivative. Alternatively the protecting group is removed and acyl shift occurs to give the derivative. These derivatives are useful in the synthesis of compounds such as peptidyl alpha-ketoamides and alpha-hydroxy-beta-carboxylic acid and amide derivatives. Certain of these compounds have been reported to have activity as inhibitors of proteases, such as serine proteases and cysteine proteases.

    专利号:US-7138526-B1
    优先权日:1999-06-15
    标 题 :Solid phase synthesis of n,n-disubstituted diazacycloalkylcarboxy derivatives
    发明人:HERPIN TIMOTHY F; MORTON GEORGE C; SALVINO JOSEPH M
    权利人:AVENTIS PHARMA INC
    摘要:A method for the solid phase synthesis of N,N-disubstituted diazacycloalkylcarboxy derivatives of general formula (I) and (II) is claimed. Examples include piperazine-2-carboxamide. The method is applicable to the synthesis or large combinatorial libraries

    专利号:US-2007179279-A1
    优先权日:2005-12-30
    标题:Methods for the synthesis of arginine-containing peptides
    发明人:CHEN LIN; ROBERTS CHRISTOPHER R
    权利人:CHEN LIN; ROBERTS CHRISTOPHER R
    摘要:Methods for the synthesis of arginine-containing peptides are provided. The methods include a step that minimizes contact of side chain protected arginine with base prior to the coupling step.

    专利号:US-4704450-A
    优先权日:1983-02-21
    标 题 :Synthesis of hpGRF(Somatocrinin) in liquid phase and intermediate peptides
    发明人:DIAZ JOSEPH; DEMARNE HENRI; RONCUCCI ROMEO; SCHMELCK PAUL-HENRY
    权利人:SANOFI SA
    摘要:The invention relates to synthesis of hpGRF (Somatocrinin) in liquid phase and to intermediate peptides, comprising: coupling, one after the other and in the order of the sequence of the GRF, the fragments in which: (a) the side acid functions of the aspartic and glutamic acids and the side amine function of the lysine are protected by protector groups stable in the conditions of deprotection of the group Boc, (b) the guanidine function of the arginine is protected by protonation, and (c) the N-terminal amino acid is protected on the amine by the Boc group; selectively eliminating the group Boc from the N-terminal amine of the peptide in phase of elongation by hydrolysis with trifluoroacetic acid, said coupling being effected in an aprotic polar solvent and eliminating, at the end of sequence, all the protector groups by hydrolysis with the aid of a 0.1 to 1M solution of methanesulfonic or trifluoromethanesulfonic acid in trifluoroacetic acid.

    专利号:US-4581168-A
    优先权日:1983-02-21
    标题:Synthesis of hpGRF (Somatocrinin) in liquid phase and intermediate peptides
    发明人:DIAZ JOSEPH; DEMARNE HENRI; RONCUCCI ROMEO; SCHMELCK PAUL-HENRY
    权利人:SANOFI SA
    摘要:The invention relates to synthesis of hpGRF (Somatocrinin) in liquid phase and to intermediate peptides, comprising:--coupling, one after the other and in the order of the sequence of the GRF, the fragments in which: (a) the side acid functions of the aspartic and glutamic acids and the side amine function of the lysine are protected by protector groups stable in the conditions of deprotection of the group Boc, (b) the guanidine function of the arginine is protected by protonation, and (c) the N-terminal amino acid is protected on the amine by the Boc group;--selectively eliminating the group Boc from the N-terminal amine of the peptide in phase of elongation by hydrolysis with trifluoroacetic acid, said coupling being effected in an aprotic polar solvent and--eliminating, at the end of sequence, all the protector groups by hydrolysis with the aid of a 0.1 to 1M solution of methanesulfonic or trifluoromethanesulfonic acid in trifluoroacetic acid.

    专利号:US-7122628-B2
    优先权日:2000-12-22
    标 题:Process for the synthesis of a peptide having a Trp residue
    发明人:JACKSON STEVEN ALLEN
    权利人:IPSEN MFG IRELAND LTD
    摘要:A process for the solid phase synthesis of a peptide having at least one thyptophan residue, wherein said method comprises temporarily protecting the indole ring of said tryptophan residue with a side chain protecting group which is labile to a base wherein said protecting group is removed during cleavage of said peptide from the solid support.

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    📌 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]: 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.
    [参考文献]: Luis Guzmán, Et Al. In Vivo Nanodetoxication For Acute Uranium Exposure. Molecules. 2015 Jun 15;20(6):11017-33.

    合成参考文献


    参考文献:10.1007/bf00916124
    摘要:Sirois P, Cadieux A. Converting enzyme activity of free airway cells. Inflammation. 1986 Sep;10(3):293–302. doi: 10.1007/bf00916124.
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