CAS: 20887-95-0; (R)-2-((Tert-Butoxycarbonyl)Amino)-3-Mercaptopropanoic Acid

该化合物是氨基酸丙酸丙酸基质的衍生物,其特点是氨基氨基组中存在一种基-丁基氧碳酸基(Boc)保护组,这种改变增强了该组的稳定性和溶性,使其在聚氨酯合成和其他有机化学应用中具有独特的再活动性和特性.Boc-L-cysteine保留了硫醇(-SH)功能组,该组对于在蛋白质和peptides中形成解冻性联结至关重要.该化合物一般是白色的对非白晶状固体,在水和甲醇等极溶溶剂中可溶.其分子结构包括一个硫磺原子,它具有独特的再活动性和特性,特别是在红化反应中.Boc-L-cysteine经常用于聚苯醚合成,并且由于能够参与各种化学反应,同时能够很容易地保护产生自由的化学防范性,因此安全数据应当作为适当的化学处理.

结构式图片

相似化合物

149270-12-2 10318-18-0 32443-99-5

上下游产品

N-α-tert-butoxycarbonyl-S-(3-nitro-2-pyridylthio)-L-cysteine tert-butyl pyridin-2-yl carbonate O-(tert-butyl) S-(pyridin-2-yl)carbonothioateB°C-Cys(Bzm)-OH -L-cysteineN-(tert-butoxycarbonyl)-S-(RS)-2-nitro-1-phenylethyl-L-cysteine Nα-tert-butyloxycarbonyl-S-2-(2,4-dinitrophenyl)ethyl-L-cysteine di-t-butoxycarbonyl-L-cystine

合成工艺路线路线简述

  • 合成目标产物 Boc-Cys-Oh 主要起始原料 L-Cysteine And Di-Tert-Butyl Dicarbonate
  • (文献来源)合成步骤主要原料 L-Cysteine 和 Di-Tert-Butyl Dicarbonate
L-半胱氨酸置于三乙胺体系中,用 水,N,N-二甲基甲酰胺 用作溶剂,化学反应 10.0H,以85%的收率获得boc-L-半胱氨酸
参考文献:叔丁基 2-吡啶碳酸酯.一种用于氨基酸叔丁氧基羰基化的有用试剂
标题:叔丁基 2-吡啶碳酸酯.一种用于氨基酸叔丁氧基羰基化的有用试剂
摘要:叔丁基 2-吡啶基碳酸酯是一种稳定的结晶化合物,被发现在氨基酸的叔丁氧基羰基化中非常有效.
Doi:10.1246/cl.1984.237

海关参考信息

专利信息


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-5731413-A
优先权日:1994-06-17
标 题:Method of synthesis of peptidyl aldehydes
发明人:WEBB THOMAS ROY; REINER JOHN EUGENE; TAMURA SUSAN YOSHIKO; RIPKA WILLIAM CHARLES; DAGNINO JR RAYMOND; NUTT RUTH FOELSCHE
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.

专利号:WO-2023169082-A1
优先权日:2022-10-24
标 题:Synthesis method and application of benzothiadiazole-1-ketone compound and derivative thereof
发明人:YI WEI; ZHOU ZHI; WU LIEXIN
权利人:UNIV GUANGZHOU MEDICAL
摘要:Disclosed in the present invention are a synthesis method and application of a benzoselenazole-1-ketone compound and a derivative thereof. Sulfoximine and the element selenium are used as raw materials, and by means of a rhodium catalysis direct C-H functionalization reaction, synthesis of a series of benzoselenazole-1-ketone compounds is achieved. The solution has the advantages of strong functional group compatibility, wide substrate universality, mild conditions, simple operations, and high efficiency and universality. Meanwhile, sulfoximine and the element selenium are used as initial raw materials, a direct C-H functionalization reaction is carried out, and by means of chiral phosphoric acid, synthesis of the chiral benzoselenazole-1-ketone compound is achieved. The application prospect is good, and a sulfydryl structure in biomacromolecules such as polypeptides, saccharides, drug molecules and proteins can be specifically marked. Good anti-SARS-CoV-2 virus activity is exhibited, a trastuzumab biological conjugate can effectively image HER 2 receptors on the cell surface, displays strong fluorescence, and can be applied to the preparation of an imaging reagent for the HER 2 receptor on the cell surface.

专利号:US-2004110228-A1
优先权日:2002-04-01
标 题:Combinatorial organic synthesis of unique biologically active compounds
发明人:MCALPINE SHELLI R; TAYLOR RACHEL E; BOLLA MEGAN L; SEGALL ANCA M
摘要:The invention provides a method for making a combinatorial library of cyclic compounds, such as Holliday junction-trapping compounds, comprising the steps of (a) obtaining a plurality of trimers according to the generic structure X 1- X 2- X 3 , wherein X 1 , X 2 and X 3 can be independently any naturally or nonnaturally occurring amino acids or peptidomimetics thereof; (b) optionally coupling a spacer S to the trimer at either end; (c) cyclizing two trimers or trimer-spacer conjugates in a head-to-tail orientation; thereby obtaining a combinatorial library of compounds, wherein the library does not include an unmodifed or naturally occurring Holliday Junction-trapping compounds. The invention additionally provides methods macrocyclic compounds that are synergimycin derivatives.

专利号:US-4388235-A
优先权日:1982-02-12
标 题:Synthesis of peptides
发明人:ORLOWSKI RONALD C; SEYLER JAY K
权利人:ARMOUR PHARMA
摘要:New peptides are disclosed which have biological activity of the same type as known calcitonins and which have a shorter amino acid chain than natural calcitonins. Also resin peptides are disclosed which may be converted to peptides having such biological activity; and processes for producing said resin peptides and said calcitonin peptides.

专利号:US-4217268-A
优先权日:1978-07-20
标 题:Synthesis of peptides
发明人:HUGHES JOHN L; LIU ROBERT C; SEYLER JAY K
权利人:HUGHES JOHN L; LIU ROBERT C; SEYLER JAY K
摘要:A new peptide is disclosed which has biological activity of the same type as known calcitonins and which has a shorter amino acid chain than natural calcitonins. Also resin peptides are disclosed which may be converted to peptides having such biological activity; and processes for producing said resin peptides and said calcitonin peptides.
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主要参考文献

[参考文献]: A Hashimoto, Et Al. Determination Of Free Amino Acid Enantiomers In Rat Brain And Serum By High-Performance Liquid Chromatography After Derivatization With N-Tert.-Butyloxycarbonyl-L-Cysteine And O-Phthaldialdehyde. J Chromatogr. 1992 Nov 6;582(1-2):41-8.
[参考文献]: Kouji Uda, Et Al. Distribution And Evolution Of The Serine/aspartate Racemase Family In Invertebrates. Amino Acids. 2016 Feb;48(2):387-402.

合成参考文献


参考文献:10.1007/s00726-005-0357-8
摘要:Morikawa A, Hamase K, Inoue T, Konno R, Zaitsu K. Alterations in D-amino acid levels in the brains of mice and rats after the administration of D-amino acids. Amino Acids. 2007 Jan;32(1):13–20. doi: 10.1007/s00726-005-0357-8.
参考文献:10.1007/s00726-012-1442-4
摘要:Ito T, Maekawa M, Hayashi S, Goto M, Hemmi H, Yoshimura T. Catalytic mechanism of serine racemase from Dictyostelium discoideum. Amino Acids. 2013 Mar;44(3):1073–84. doi: 10.1007/s00726-012-1442-4.
参考文献:10.1038/s41557-018-0041-8
摘要:Wadzinski TJ, Steinauer A, Hie L, Pelletier G, Schepartz A, Miller SJ. Rapid phenolic O-glycosylation of small molecules and complex unprotected peptides in aqueous solvent. Nature Chemistry. 2018 Apr 30;10(6):644–52. doi: 10.1038/s41557-018-0041-8.
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