CAS: 39161-84-7; 4-Mercaptophenylacetic Acid

该化合物是一种有机化合物,其特征是带有硫醇(-SH)组和联苯环的碳酸(-COOH)组,该化合物一般是白色的,白色的固体,因其功能组而溶解于极地溶剂中.硫醇组具有独特的再活动性,可以形成脱硫联系并参与各种化学反应,包括核嗜好替代和红氧化反应.箱酸组有助于其酸性,可以参与氢结合,提高其在水中的溶液性.4-甲基苯乙酸经常用于有机合成,特别是在制药业中和作为制造更复杂的分子的建筑块.此外,硫醇组的功能使其在生物凝聚和材料科学应用中具有价值,例如改变表面和生成硫醇-乙烯聚合物.

结构式图片

欧盟法规

ECHA物质C&L通报

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CAS号1197-55-3 对氨基苯乙酸 | CAS号317319-11-2 methyl 2-(4-((d... | CAS号14199-15-6 对羟基苯乙酸甲酯 | CAS号477256-87-4 methyl 2-(4-((d... | CAS号383135-47-5 4-乙基磺酰基苯乙酸 | CAS号5325-76-8 2,2-(Dithiobis(...

合成工艺路线路线简述

    4-羟基苯乙酸甲酯置于三乙烯二胺,氢氧化钾体系中,用 甲醇,N,N-二甲基甲酰胺 作为反应溶剂,化学反应生成 4-巯基苯基乙酸
    参考文献:芳香族硫醇对蛋白质折叠过程中发生的硫醇-二硫键交换反应的影响.
    标题:芳香族硫醇对蛋白质折叠过程中发生的硫醇-二硫键交换反应的影响.
    摘要:包含二硫键的蛋白质从变性蛋白质到天然蛋白质的折叠涉及许多硫醇-二硫键交换反应.这些反应中的许多反应都包含氧化还原缓冲液,该缓冲液是硫醇(rsh)和相应的二硫键(rssr)的混合物.rsh的结构与其在体外折叠蛋白中的功效之间的关系仅在有限的范围内进行了研究.本文报道了脂族和尤其是芳族硫醇对蛋白质折叠期间发生的反应的影响.芳族硫醇可能特别有效,因为它们的硫醇pk(a)值和反应性与体内催化剂蛋白质二硫键异构酶(pdi)匹配.这项研究将芳香族硫醇的硫醇pk(a)值与其对小分子二硫键和蛋白质胰岛素的反应性相关联.测量了九种对位取代的芳族硫醇的硫醇pk(a)值;使用sigma(p-)值构建的hammett图得出rho =-1.6 +/-0.1.测定了芳香族和脂肪族硫醇与2-吡啶基二硫代乙醇(2-Pde)(一种小分子二硫化物)的反应性.芳族硫醇的反应性与pk(a)的关系图的斜率(β)为0.9.这些硫
    DOI:10.1021/jo015600A

    海关参考信息

    专利信息


    专利号:WO-2024165450-A1
    优先权日:2023-02-09
    标题:Method of chemical synthesis of single-chain antibody fragments and products thereby obtained
    发明人:FIGINI MARIANGELA; LUISON ELENA
    权利人:GLYTECH INC; FIGINI MARIANGELA
    摘要:A new method is disclosed for the protein full-chemical synthesis of single-chain antibody fragments (scFv); the obtained products are structurally close and functionally equivalent to their biological counterpart, being however, advantageously free of impurities and more reproducible in properties. The method includes the general steps of: (a) separately synthetizing sub-sequences (peptide fragments) (b) sequentially assembling the sub-sequences obtained in step (a) in the order as they appear in the target scFv amino acid sequence, and (c) performing oxidative folding of the assembled whole peptide molecule obtained in step (b) and dialyzing the resulting product in a buffer.

    专利号:US-8404804-B2
    优先权日:2007-08-28
    标 题 :Methods and intermediates for chemical synthesis of polypeptides and proteins
    发明人:DONG ZHENG XIN; EYNON JOHN S
    权利人:DONG ZHENG XIN; EYNON JOHN S; IPSEN PHARMA SAS
    摘要:The present invention relates to methods and intermediates for chemical synthesis of polypeptides and proteins, and more particularly to methods and intermediates for chemically ligating a peptide fragment containing N-terminal N-methyl-cysteine (SEQ ID NO: 1) with another peptide fragment having C-terminal thioester to generate a β-(methylamino)-thioester intermediate that spontaneously rearranges to form an amide bond. Furthermore, the invention relates to methods of converting N-methyl-thiazolidine to N-methyl-cysteine (SEQ ID NO: 1) of polypeptides and proteins. The invention also relates to methods of synthesizing peptide-thioester from peptide-acid fluoride.

    专利号:US-2010204449-A1
    优先权日:2007-09-04
    标 题 :Methods and intermediates for chemical synthesis of polypeptides and proteins
    发明人:DONG ZHENG XIN; KIM SUN H
    权利人:DONG ZHENG XIN; KIM SUN H
    摘要:The present invention relates to methods and intermediates for chemical synthesis of polypeptides and proteins, and more particularly to methods and intermediates for chemically ligating a peptide fragment containing N-terminal β-methyl-cysteine (SEQ ID NO: 1) with another peptide fragment having C-terminal thioester to generate a β-amino-thioester intermediate that spontaneously rearranges to form an amide bond. The invention also relates to methods of synthesizing β-methyl-cysteine (SEQ ID NO: 1) and its protected forms. Furthermore, the invention relates to converting a β-methyl-thiazolidine residue to a β-methyl-cysteine (SEQ ID NO: 1) residue of polypeptides and proteins.

    专利号:US-2020190135-A1
    优先权日:2016-11-16
    标题 :Lasso structures and their synthesis
    发明人:BODE JEFFREY; SAITO FUMITO
    权利人:CHROMACON AG
    摘要:A method for the synthesis of a molecular lasso structure in which a linear moiety is covalently attached to a cyclic moiety and with its free end is partially threaded through the orifice formed by the cyclic moiety, including the following steps: 1) provision of a cyclic and a first linear structural element and establishing conditions in which the first linear structural element is threaded through the orifice of the cyclic moiety; 2) covalently attaching a stopper element to one terminal end of the linear structural element; 3) separating unthreaded from threaded molecular assemblies by chemical or physical separation; and 4) reacting the threaded molecular assemblies with a second linear structural element so that it is covalently attached to the first linear structural element at its end opposite to the end where the stopper is attached, and so that the second linear structural element is covalently attached to the cyclic moiety.

    专利号:US-9850275-B2
    优先权日:2013-09-11
    标 题 :Photolabile linker for the solid-phase synthesis of hydrazides and pyranopyrazoles
    发明人:NIELSEN THOMAS E; QVORTRUP KATRINE
    权利人:UNIV DANMARKS TEKNISKE
    摘要:The photolabile hydrazine linker of the present invention is based on the o-nitro-veratryl group, which is capable of releasing hydrazide derivatives upon UV irradiation. The linker allows for a new solid-phase peptide synthesis (SPPS) strategy which is fully orthogonal to the most commonly used protecting groups and chemical methods in SPPS and shows excellent compatibility with peptide composition, notably the 20 naturally occurring α-amino acid residues (even in their side-chain protected form) are accepted in the C-terminal of the peptide hydrazides. Furthermore, the linker unit can be applied to synthesize combinatorial libraries of biological interesting heterocyclic compounds, such as pyranopyrazoles.

    专利号:US-2022233673-A1
    优先权日:2019-06-04
    标 题:METHODS OF PRODUCING SHIGA TOXIN B-SUBUNIT (STxB) MONOMERS AND OLIGOMERS, AND USES THEREOF
    发明人:BILLET ANNE; SCHMIDT FRÉDÉRIC; JOHANNES LUDGER; SERVENT DENIS; MOURIER GILLES; TARTOUR ÉRIC; KAY MICHAEL; FULCHER JAMES M
    权利人:INST CURIE; CENTRE NAT RECH SCIENT; INST NAT SANTE RECH MED; COMMISSARIAT A LENERGIE ATOMIQUE ET AUX ENERGIES ALTERNATIVES CEA; APHP ASSIST PUBLIQUE HOPITAUX DE PARIS; UNIV PARIS; UNIV OF UTAH RESEARCH FOUDATION; UNIV UTAH RES FOUND
    摘要:A method of producing a monomer of a Shiga toxin B-subunit (STxB) protein or of a variant thereof by peptide chemical synthesis, as well as to a method of producing a pentamer of the STxB protein or of the variant thereof. The methods are particularly advantageous as they overcome major issues typically observed in peptide chemical synthesis, including solubility and purity issues.
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    主要参考文献

    [参考文献]: Daniel J Capon, Et Al. Flexible Antibodies With Nonprotein Hinges. Proc Jpn Acad Ser B Phys Biol Sci. 2011;87(9):603-16.
    [参考文献]: Paul W R Harris, Et Al. Chemical Synthesis Of A Polypeptide Backbone Derived From The Primary Sequence Of The Cancer Protein Ny-Eso-1 Enabled By Kinetically Controlled Ligation And Pseudoprolines. Biopolymers. 2015 Mar;104(2):116-27.

    合成参考文献


    摘要:Malins, L. R.; Payne, R. J., Science of Synthesis Knowledge Updates, (2021) 3, 195.
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