CAS: 1234-35-1; Z-Arg-Oh

该化合物是氨基酸乙基氨基氨酸保护组的衍生物,其特点是存在苯氧基碳基(Z)保护组,该化合物通常在丙二酸合成中用作氨基丙基氨氨基磺酸的保护组,以便利氨基硫酸在形成peptides过程中选择性地结合,Z组在合成过程中增强氨基乙酸的稳定性,同时允许随后在温和条件下进行去保护.苯丙基碳酸-L-氨基因通常是一种白到白的晶状固体,在二甲基硫氧化物和甲醇等有机溶剂中溶解,但在水中溶液较少.该化合物的分子结构包括一个促进其基本性和再活性的基亚胺组.该混合物在生物化学研究和药物应用方面占有重要地位,特别是在开发基于丙基药物和研究蛋白相互作用方面.与许多化学物质一样,适当的处理和储存对于在实验室环境中保持其完整性和有效性至关重要.

结构式图片

相似化合物

56672-63-0 6382-93-0 1119-34-2

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合成工艺路线路线简述

  • 合成目标产物 Nalpha-Cbz-L-Arginine 主要起始原料 Cyanamide And Z-Orn-Oh
  • (文献来源)合成步骤主要原料 Cyanamide 和 Z-Orn-Oh
Nα-Cbz-Nω-硝基-L-精氨酸置于copper Acetylacetonate,Sodium Tetrahydroborate体系中,用 乙醇 用作溶剂,化学反应 2.0H,反应生成N-苄氧羰基-L-精氨酸
参考文献:Nabh4-A Novel Method For The Deprotection Of Nω-Nitro-Arginine
标题:Nabh4-A Novel Method For The Deprotection Of Nω-Nitro-Arginine
摘要:The Selective Deprotection Of N-Omega-Nitro-Arginine Derivatives Represents A Major Preparative Challenge. This Problem Can Be Circumvented By The Use Of Catalytic Hydrogenation,But Often High Pressure,Elevated Temperature,And/or Long Reaction Times Are Needed. In Certain Cases Hydrogenation Is Not Suitable,For Example,Small-Scale Reactions,Parallel Synthesis,Or Due To Selectivity Issues. Herein,We Demonstrate For The First Time,The Use Of Nabh4 In The Presence Of A Metal Ion Catalyst For The Removal Of The N-Omega-Nitro Moiety Under Simple,'Open-Vessel' Conditions. This Process Using Nabh4 Does Not Remove The Benzyloxycarbonyl-Protecting Group; Thus The Method Is Orthogonal For This Protecting Scheme. (C) 2015 Elsevier Ltd. All Rights Reserved.
Doi:10.1016/j.Tetlet.2015.12.081

海关参考信息

专利信息


专利号:WO-2010103857-A1
优先权日:2009-03-12
标 题 :Method for solid-phase synthesis of glycopeptide using silicon-containing protecting group and synthesis device
发明人:NISHIMURA SHIN-ICHIRO; SHIMAWAKI KEN
权利人:UNIV HOKKAIDO NAT UNIV CORP; NISHIMURA SHIN-ICHIRO; SHIMAWAKI KEN
摘要:Disclosed are a novel method for the synthesis of a glycopeptide by which glycopeptides of various types can be deprotected and excised from a resin, each under weakly acidic to weakly basic conditions, without causing the problems of the epimerization of an amino acid at the a-position and the ß-elimination of a sugar residue; a synthesis device therefor; and a synthesis intermediate to be used in synthesizing a glycopeptide. Specifically disclosed are a method for the solid-phase synthesis of a glycopeptide which comprises a step for obtaining a glycopeptide derivative wherein the N-terminus is protected, the C-terminus is immobilized to a solid phase via a silicon linker, and a reactive group carried by a sugar residue and a reactive group carried by an amino acid side chain constituting a peptide are protected by silicon-containing groups, and a step for obtaining the glycopeptide by deprotecting said glycopeptide derivative and releasing the same from the solid phase by treating the glycopeptide derivative with an agent for removing the silicon-containing groups and the silicon linker; a synthesis intermediate to be used in the step for obtaining the glycopeptide derivative in the aforesaid method; and a device for the solid-phase synthesis of a glycopeptide.

专利号:EP-0790982-B1
优先权日:1994-06-17
标 题 :Methods of synthesis of peptidyl argininals
发明人:WEBB THOMAS R; REINER JOHN E; TAMURA SUSAN Y; RIPKA WILLIAM C; DAGNINO RAYMOND JR; NUTT RUTH F
权利人:CORVAS INT INC
摘要:This invention provides solution-phase and solid-phase methods for the synthesis of peptidyl argininals and to novel reagents useful therein, which have formula (I), wherein R1 is selected from the group consisting of hydrogen, benzyloxycarbonyl, isonicotinyloxycarbonyl, 2-chlorobenzyloxycarbonyl, 4-methoxybenzyloxycarbonyl, t-butoxycarbonyl, t-amyloxycarbonyl, isobornyloxycarbonyl, adamantyloxycarbonyl, 2-(4-biphenyl)-2-propyloxycarbonyl, 9-fluorenylmethoxycarbonyl and methylsulfonylethoxycarbonyl; R2 is selected from the group consisting of alkyl of 1 to about 12 carbon atoms and aralkyl of about 7 to about 15 carbon atoms, either of which is optionally substituted with hydroxy or -CO-Y, wherein Y is hydroxy, alkoxy of 1 to about 12 carbon atoms, aralkoxy of about 7 to about 15 carbon atoms, O-polymeric support or NH-polymeric support; R3 is selected from the group consisting of hydrogen, Fmoc, nitro, benzyloxycarbonyl, t-butoxycarbonyl and adamantyloxycarbonyl; and R4 is selected from the group consisting of hydrogen, alkyl of 1 to about 12 carbon atoms, aryl of about 6 to about 14 carbon atoms and aralkyl of about 7 to about 15 carbon atoms; and salts thereof.

专利号:US-5342970-A
优先权日:1991-05-30
标 题 :Hydrosoluble coumarin derivatives, their preparation and their use as an enzyme substrate or for the preparation of such substrates
发明人:CHALOM JOSEPH; GRIFFOUL CHRISTINE; TOD MICHEL; REVEILLEAU STEPHANE
权利人:EUROBIO LAB
摘要:The invention relates to hydrosoluble coumarin derivatives. These derivatives comply with the formula: (I) in which R1 represents (OCH2CH2)mOCH2R7 or (OCH(CH3)CH2)mOCH2R7 with m=1 to 30 and in which R7 can be a hydrogen atom or various groups, R2 to R6 can be different substituents, particularly substituents making it possible to introduce into the derivative an appropriate group as the enzyme substrate or for the synthesis of enzyme substrates.

专利号:WO-2024146948-A1
优先权日:2023-01-05
标题:Peptide synthesis method involving sterically hindered tri-tert-butyl-tryptophan (tbt) residue
发明人:EKSTEEN JACOBUS JOHANNES; SVENDSEN JOHN SIGURD; MALMEDY FLORENCE; GUEVARA JONATHAN
权利人:AMICOAT AS
摘要:The invention is directed to a method of peptide synthesis comprising reacting a compound of Formula (I) or a salt thereof with a carbodiimide reagent to form an O-acylisourea intermediate; reacting the O-acylisourea intermediate with an additive to form an activated ester; and reacting the activated ester with an amino-containing moiety which is an amino acid, a peptide or a salt thereof comprising an amino group, wherein the amino group forms an amide bond with the carbonyl marked * in Formula (I); wherein the compound of Formula (I) has the structure: and wherein R1 and R2 are as defined in the disclosure. The invention is also directed to a compound of Formula (III) as defined in the disclosure or a salt thereof.

专利号:WO-9535280-A1
优先权日:1994-06-17
标 题:Methods of synthesis of peptidyl argininals

专利号:US-3862113-A
优先权日:1972-09-22
标 题 :Process for the selective elimination of aralkyloxycarbonyl and trityl n-protecting groups with 2,2,2-trifluoroethanol
发明人:RINIKER BERNHARD; KAMBER BRUNO; SIEBER PETER
权利人:CIBA GEIGY CORP
摘要:A process for the selective elimination of amino protective groups in peptide synthesis, wherein the trityl group and/or an aralkyloxycarbonyl group such as the 2-(p-bi-phenylyl)-2propyloxycarbonyl group is (are) split off in trifluorethanol at a pH of about 4 or 1, respectively.
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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:10.1271/bbb.70741
摘要:ZHU B, ZHAO L, SUN L, LI D, MURATA Y, YU L, ZHANG L. Purification and Characterization of a Cathepsin L-Like Enzyme from the Body Wall of the Sea CucumberStichopus japonicus. Bioscience, Biotechnology, and Biochemistry. 2008 Jun 23;72(6):1430–7. doi: 10.1271/bbb.70741.
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