CAS: 7432-21-5; (S)-2-(((Benzyloxy)Carbonyl)Amino)-3-(1H-Indol-3-yl)Propanoic Acid

该化合物是氨酸酸锥体的衍生物,其特点是存在苯氧基碳基(Z)保护组.这种化合物通常用于peptide合成,作为氨酸锥体组的保护群体,促进形成peptide 债券,不受氨基聚物集团的干扰.它是白到白的固体,在二甲基硫氧化物(DMSO)和甲醇等有机溶剂中溶解,但在水中溶解性有限.苯氧基碳基组的存在加强了氨酸在化学反应期间的稳定性,使其成为有机合成和制药应用中的宝贵中间体.此外,N-苯氧基碳基-L-trypophophan可以在特定条件下进行水解,释放自由氨基酸,这对各种生物功能,包括蛋白合成和...

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benzyl chloroformate L-Tryptophan N-α-carbobenzoxy-L-tyrosine p-nitrophenyl ester dibenzyl dicarbonateNα-benzyloxycarbonyl-tryptophan)-[5']inosinic acid-anhydride(Nα-benzyloxycarbonyl-tryptophan)-[5']inosinic acid-anhydride Z-Trp-Gly-Gly-OH N-carbobenzyloxy-L-tryptophanyl-L-isoleucine methyl ester S-benzyl-N-(Nα-benzyloxycarbonyl-L-tryptophyl)-L-cystein-ethyl esterS-benzyl-N-(Nα-benzyloxycarbonyl-L-tryptophyl)-L-cystein-ethyl ester

合成工艺路线路线简述

    (S)-N-Benzyloxycarbonyl-L-Tryptophan Methyl Ester置于水,Lithium Hydroxide,盐酸体系中,用 四氢呋喃,水 作为反应溶剂,化学反应 3.0H,反应生成 N-苄氧羰基-L-色氨酸
    参考文献:色氨酸-六氢吡咯并吲哚合成中的正交保护基团
    标题:色氨酸-六氢吡咯并吲哚合成中的正交保护基团
    摘要:此处描述了在六氢吡咯并 [2,3-B] 吲哚和吲哚色氨酸之间包含 Ac3A-Ni 键的各种多环系统的合成.进行了一系列实验以确定五个正交保护基团的最佳组合和形成所述键的最佳反应条件,这是许多最近发现的海洋天然产物的共同特征.
    DOI:10.1002/ejoc.201101057

    海关参考信息

    专利信息


    专利号:US-7435791-B2
    优先权日:2001-07-19
    标题:Process for rapid solution synthesis of peptides
    发明人:EGGEN IVO FRANCI; TEN KORTENAAR PAULUS BERNARDUS; HAASNOOT CORNELIS ALBERT GRUSON
    权利人:ORGANON NV
    摘要:The present invention relates to a process for rapid solution synthesis of a peptide, the process comprising repetitive cycles of steps (a)-(d):n (a) a coupling step, using an excess of an activated carboxylic component to acylate an amino component, (b) a quenching step in which a scavenger is used to remove residual activated carboxylic functions, wherein the scavenger may also be used for deprotection of the growing peptide, (c) one or more aqueous extractions and optionally, (d) a separate deprotection step, followed by one or more aqueous extractions, characterised in that the process comprises at least one step (b), referred to as step (b′), in which an amine or a thiol comprising a free anion or a latent anion is used as a scavenger of residual activated carboxylic functions. nn During the process of this invention the growing peptide need not be isolated until the final peptide sequence has been obtained. n This highly efficient process is useful for the production of oligo- and polypeptides of high purity.

    专利号:US-11414375-B2
    优先权日:2016-07-29
    标题:Mild and efficient preparation method for α-acyloxyenamide compounds and use thereof in synthesis of amide and polypeptide
    发明人:ZHAO JUNFENG; HU LONG; XU SILIN; ZHAO ZHENGUANG
    权利人:UNIV JIANGXI NORMAL
    摘要:Disclosed are a mild and efficient preparation method for an α-acyloxyenamide compound and a use thereof in the synthesis of an amide and a polypeptide. The α-acyloxyenamide compound is obtained by an addition reaction of a ynamide and a carboxylic acid in dichloromethane under conditions where the temperature is 0° C. to 50° C.; the produced α-acyloxyenamide compound can react with an amine compound to produce an amide or a polypeptide; the two reactions can be carried out step by step, and can also be carried out in one pot. According to the invention, the reaction conditions are mild and no metal catalyst is required; when the carboxylic acid, which has chirality on an alpha site of carboxyl, forms an amide bond or a peptide bond, no racemization occurs; and the operation is simple and the application range is wide.

    专利号:US-2024218014-A1
    优先权日:2022-11-21
    标 题:Synthesis of a cyclic peptide
    发明人:BAUR PIUS BRUNO; CLEATOR EDWARD; DENIAU GILDAS; EISELE FRANK; FLÖGEL OLIVER; HUSTE ANJA; KEHL MARCEL ROMAN; LÖWENECK MARKUS; SILVA ROLANDO RAVELO; VORBERG RAFFAEL
    权利人:JANSSEN PHARMACEUTICA NV
    摘要:Processes for performing peptide synthesis, particularly for cyclic peptide synthesis are generally described. Reaction intermediates of the peptide synthesis are also described.

    专利号:US-2023220001-A1
    优先权日:2020-06-09
    标 题:Method for synthesis of thioether-containing peptides
    发明人:GRUSS HENDRIK; LUTZ CHRISTIAN; SÜSSMUTH RODERICH; Yao guiyang; KNITTEL CAROLINE; KOSOL SIMONE; MAINZ ANDI
    权利人:HEIDELBERG PHARMA RES GMBH
    摘要:The present invention relates to a method of formation of a sulphur bridge between tryptophan and cysteine in solid phase peptide synthesis under iodine treatment. The invention also relates to the resulting compounds of the method and their respective use.

    专利号:US-3953416-A
    优先权日:1971-12-20
    标 题:Synthetic decapeptide having the activity of the luteinizing hormone releasing hormone and method for manufacturing the same
    发明人:FOLKERS KARL; CURRIE BRUCE L; CHANG JAW-KANG; SIEVERTSSON HANS; BOGENTOFT CONNY
    权利人:FOLKERS KARL; CURRIE BRUCE L; CHANG JAW KANG; SIEVERTSSON HANS; BOGENTOFT CONNY
    摘要:A synthetic decapeptide, L-pglutamyl-L-histidyl-L-tryptophanyl-L-seryl-L-tyrosyl-glycyl-L-leucy l-L-arginyl-L-prolyl-glycinamide which has the hormonal activities of the luteinizing hormone releasing hormone (LRH) of the hypothalamus gland of mammals is produced by utilizing as the key starting materials, the amino acids, glutamic acid or pyroglutamic acid, histidine, tryptophan, serine, tyrosine, glycine, leucine, arginine, and proline. Synthesis of the decapeptide is accomplished by coupling, in appropriate combinations of appropriate protected forms of the amino acids, and finally deprotecting to yield the amide, L-pglutamyl-L-histidyl-L-tryptophanyl-L-seryl-L-tyrosyl-glycyl-L-leucy l-L-arginyl-L-prolyl-glycinamide.

    专利号:BR-PI0202783-B1
    优先权日:2001-07-19
    标 题:process for the rapid synthesis of a peptide in solution in an organic solvent or a mixture of organic solvents, and methods for the combinatorial synthesis of peptide collections and for automated solution peptide synthesis
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    主要参考文献

    参考标题:A Facile Synthesis Of Hydroxamic Acids OfNα-Protected Amino Acids Employing Bdms, A Study Of Their Molecular Docking And Their Antibacterial Activities
    作者:K. Uma,H. S. Lalithamba,V. Chandramohan,K. Lingaraju |发布日期:2019.3.4
    摘要:Hydroxamic Acids Have Received Much Attention As Biologically Active Compounds. Synthetic Hydroxamic Acids Enhance The Growth Of Plant Sources And Improve The Soil Quality, Act As Antibiotics, Cell...

    合成参考文献


    参考文献:10.1016/0006-8993(85)90764-4
    摘要:Vigna SR, Szecòwka J, Williams JA. Do antagonists of pancreatic cholecystokinin receptors interact with central nervous system cholecystokinin receptors Brain Res. 1985 Sep 23;343(2):394–7. doi: 10.1016/0006-8993(85)90764-4.
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