CAS: 618-27-9; (2S,4S)-4-Hydroxypyrrolidine-2-Carboxylic Acid

该化合物是一种氨酸衍生物,具有独特的结构特征和立体化学特征,是一种循环化合物,特别是一种丙醇衍生物,附于脊柱第四碳的氢氧基(OH)组.这种配置有助于其特性,包括其在蛋白质结构和功能中的作用,特别是在科洛伦合成中的作用."cis"标志表明,氢氧基和相邻碳链位于分子的同一面,影响其空间安排和再活动.Cis-4-Hydroxy-L-proline因其潜在的生物活动而闻名,包括参与稳定科朗三叶类肝和对细胞过程的影响.这种配置在水中可溶化,并展示出可参与氢结合的氢氧基组的极性.这种化合物对生物化学研究和药物应用都有兴趣,特别是在研究与科洛根有关的紊乱和治疗剂的开发中.

结构式图片

相似化合物

441067-49-8 6912-67-0 13504-85-3

欧盟法规

ECHA物质C&L通报REACH预注册

上下游产品

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合成工艺路线路线简述

  • 合成目标产物 Cis-4-Hydroxy-L-Proline 主要起始原料 Z-Cis-Hyp-Oh
  • (文献来源)合成步骤主要原料 Z-Cis-Hyp-Oh
N-乙酰-L-4-羟基脯氨酸置于1,4-二氧六环,吡啶,盐酸,Sodium Hydroxide,乙醚体系中,化学反应生成 顺式-4-羟基-L-脯氨酸
参考文献:Neuberger,Journal Of The Chemical Society,1945,P. 431
标题:Neuberger,Journal Of The Chemical Society,1945,P. 431

海关参考信息

专利信息


专利号:US-7589170-B1
优先权日:1998-09-25
标题 :Synthesis of cyclic peptides
发明人:SMYTHE MARK LESLIE; MEUTERMANS WIM DENIS FRANS; BOURNE GREGORY THOMAS; MCGEARY ROSS PETER
权利人:UNIV QUEENSLAND
摘要:This invention relates to methods for preparing cyclic peptides and peptidomimetic compounds in solution and bound to solid supports, and to cyclic peptide or peptidomimetic libraries for use in drug screening programs. In particular, the invention relates to a generic strategy for synthesis of cyclic peptides or peptidomimetics that enables the efficient synthesis under mild conditions of a wide variety of desired compounds. Two approaches were evaluated for their improvements in solution and solid phase synthesis of small cyclic peptides: positioning reversible N-amide substituents in the sequence; and applying native ligation chemistry in an intramolecular sense. Systematic investigation of the effects of preorganising peptides prior to cyclisation by using peptide cyclisation auxiliaries, and developing new linkers and peptide cyclisation auxiliaries to aid cyclic peptide synthesis gives surprising improvements in both yields and purity of products compared to the prior art methods. The combination of these technologies provides a powerful generic approach for the solution and solid phase synthesis of small cyclic peptides. The ring contraction and N-amide substitution technology of the invention provide improved methods for the synthesis of cyclic peptides and peptidomimetics. When used in conjunction with linker strategies, this combination provides solid-phase avenues to cyclic peptides and peptidomimetics.

专利号:US-12188072-B2
优先权日:2018-03-19
标题 :Compositions and methods for rapid in vitro synthesis of bioconjugate vaccines in vitro via production and N-glycosylation of protein carriers in detoxified prokaryotic cell lysates
发明人:JEWETT MICHAEL CHRISTOPHER; STARK JESSICA CAROL; DELISA MATTHEW P; JAROENTOMEECHAI THAPAKORN
权利人:UNIV NORTHWESTERN; UNIV CORNELL
摘要:Disclosed are methods, systems, components, and compositions for cell-free synthesis of glycosylated carrier proteins. The glycosylated carrier proteins may be utilized in vaccines, including anti-bacterial vaccines. The glycosylated carrier proteins may include a bacterial polysaccharide conjugated to a carrier, which may be utilized to generate an immune response in an immunized host against the polysaccharide conjugated to the carrier. The glycosylated carrier proteins may be synthesized in cell-free glycoprotein synthesis (CFGpS) systems using prokaryote cell lysates that are enriched in components for glycoprotein synthesis such as oligosaccharyltransferases (OSTs) and lipid-linked oligosaccharides (LLOs) including OSTs and LLOs associated with synthesis of bacterial O antigens.

专利号:US-12365930-B2
优先权日:2016-07-14
标题:Method for rapid in vitro synthesis of glycoproteins via recombinant production of N-glycosylated proteins in prokaryotic cell lysates
发明人:JEWETT MICHAEL CHRISTOPHER; STARK JESSICA CAROL; DELISA MATTHEW P; JAROENTOMEECHAI THAPAKORN
权利人:UNIV NORTHWESTERN; UNIV CORNELL
摘要:Disclosed are methods, systems, components, and compositions for cell-free synthesis of glycosylated proteins. The glycosylated proteins may be utilized in vaccines, including anti-bacterial vaccines. The glycosylated proteins may include a bacterial polysaccharide conjugated to a carrier, which may be utilized to generate an immune response in an immunized host against the polysaccharide conjugated to the carrier. The glycosylated proteins may be synthesized in cell-free glycoprotein synthesis (CFGpS) systems using prokaryote cell lysates that are enriched in components for glycoprotein synthesis such as oligosaccharyltransferases (OSTs) and lipid-linked oligosaccharides (LLOs) including OSTs and LLOs associated with synthesis of bacterial O antigens.

专利号:US-7344863-B2
优先权日:1998-03-13
标题:Methods for producing polypeptides through enhanced synthesis of encoding nucleic acid molecules
发明人:LI WU-BO; JESSEE JOEL A; SCHUSTER DAVID; XIA JIULIN; GEBEYEHU GULILAT
权利人:INVITROGEN CORP
摘要:The present invention is directed to compositions and methods for enhancing synthesis of nucleic acid molecules, particularly GC-rich nucleic acid molecules. Specifically, the invention provides compositions comprising one or more nitrogen-containing organic compounds having a formula selected from the group consisting of formula I and formula II (or salts or derivatives thereof), preferably 4-methylmorpholine N-oxide or betaine (carboxymethyltrimethylammonium), and further comprising one or more compounds selected from the group consisting of proline and an N-alkylimidazole compound, and more preferably proline, 1-methylimidazole or 4-methylimidazole. The invention further relates to methods for enhanced, high-fidelity synthesis of nucleic acid molecules, including via amplification (particularly PCR), reverse transcription, and sequencing methods. The invention also relates to nucleic acid molecules synthesized by these methods, to fragments or derivatives thereof, and to vectors and host cells comprising such nucleic acid molecules, fragments, or derivatives. The invention also relates to kits for synthesizing, amplifying, reverse transcribing or sequencing nucleic acid molecules comprising one or more of the compositions of the invention.

专利号:US-2022298204-A1
优先权日:2019-07-05
标题 :Synthesis of a-amanitin and its derivatives
发明人:SIEGERT MARY-ANN; KNITTEL CAROLINE HERTA; SÜSSMUTH RODERICH
权利人:PURE BIOORGANICS SIA
摘要:The present invention relates to the chemical synthesis of α-amanitin and its derivatives. The present invention also relates to intermediate products of the α-amanitin synthesis.

专利号:US-5549974-A
优先权日:1994-06-23
标题:Methods for the solid phase synthesis of thiazolidinones, metathiazanones, and derivatives thereof
发明人:HOLMES CHRISTOPHER P
权利人:AFFYMAX TECH NV
摘要:The invention provides an efficient and versatile method for the combinatorial synthesis and screening of libraries of 4-thiazolidinones, metathiazanones, and derivatives thereof. In order to expediently synthesize a combinatorial library of derivatives based upon these core structures, a general methodology for the solid phase synthesis of these derivatives is also provided. Arrays of thiazolidinones, metathiazanones, and derivatives thereof useful as peptidomimetics and for the identification of agents having antifungal, antihistaminic, or antimicrobial activity or use in the treatment of inflammation, hypertension, renal failure, congestive heart failure, uremia and other conditions can be prepared using this method.
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主要参考文献

[参考文献]: Kao Ww, Et, Al. Proline Analogue Removes Fibroblasts From Cultured Mixed Cell Populations. Nature. 1977 Mar 3;266(5597):63-4.
[参考文献]: Lewko Wm, Et, Al. Sensitivity Of N-Nitrosomethylurea-Induced Rat Mammary Tumors To Cis-Hydroxyproline, An Inhibitor Of Collagen Production. Cancer Res. 1981 Jul;41(7):2855-62.
[参考文献]: Riley Dj, Et, Al. Prevention Of Bleomycin-Induced Pulmonary Fibrosis In The Hamster By Cis-4-Hydroxy-L-Proline. Am Rev Respir Dis. 1981 Apr;123(4 Pt 1):388-93.
[参考文献]: Tan Em, Et, Al. Proline Analogues Inhibit Human Skin Fibroblast Growth And Collagen Production In Culture. J Invest Dermatol. 1983 Apr;80(4):261-7.
[参考文献]: Beata A Butruk-Raszeja, Et Al. Athrombogenic Hydrogel Coatings For Medical Devices--Examination Of Biological Properties. Colloids Surf B Biointerfaces. 2015 Jun 1:130:192-8.

合成参考文献


摘要:Vicens, L.; Borrell, M.; Costas, M., Science of Synthesis: Catalytic Oxidation in Organic Synthesis, (2017) 1, 125.
参考文献:10.1186/s12931-015-0283-6
摘要:Nickler M, Ottiger M, Steuer C, Huber A, Anderson JB, Müller B, Schuetz P. Systematic review regarding metabolic profiling for improved pathophysiological understanding of disease and outcome prediction in respiratory infections. Respiratory Research. 2015 Oct 15;16(1):125. doi: 10.1186/s12931-015-0283-6.
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