CAS: 15871-57-5; 2,2,6,6-Tetramethylpiperidine-N-Oxyl-4-Amino-4-Carboxylic Acid

该化合物是一个稳定的硝基氧化基基,其独特结构特征是包括氨基和碳酸基酸功能组的管状环在内的一个独特的结构,该化合物具有显著的抗氧化性特性,在各种生物化学应用中,包括在氧化压力和细胞信号研究中,具有有用的作用.TEMPOL在水和有机溶剂中溶解,这增强了其在实验环境中的多功能.其激进性质使其得以参与红氧化反应,有效地挽救了自由基,并有可能减轻细胞损害.此外,TEMPOL因其独特的化学特性和生物活动,其治疗潜力都受到调查,包括心血管疾病和...

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37149-18-1 14691-88-4 14691-89-5

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CAS号15871-56-4 外消旋-2,2,6,6-四甲基... | CAS号93372-25-9 FM°C-2,2,6,6-TE...

合成工艺路线路线简述

  • 合成目标产物 2,2,6,6-Tetramethylpiperidine-1-Oxyl-4-Amino-4-Carboxylic Acid 主要起始原料 Rac-2,2,6,6-Tetramethylpiperidine-N-Oxyl-4, 4-(5-Spirohydantoin)
  • (文献来源)合成步骤主要原料 Rac-2,2,6,6-Tetramethylpiperidine-N-Oxyl-4, 4-(5-Spirohydantoin)
📜7,7,9,9-Tetramethyl-2,4-Dioxo-1,3,8-Triaza-Spiro[4.5]Dec-8-Yloxyl置于barium Dihydroxide体系中,化学反应 48.0H,以92%的收率获得2,2,6,6-四甲基吡啶-1-氧基-4-氨基-4-羧酸
参考文献:Smythe,Mark L.; Nakaie,Clovis R.; Marshall,Garland R.,Journal Of The American Chemical Society,1995,Vol. 117,# 42,P. 10555-10562
标题:Smythe,Mark L.; Nakaie,Clovis R.; Marshall,Garland R.,Journal Of The American Chemical Society,1995,Vol. 117,# 42,P. 10555-10562

海关参考信息

专利信息


专利号:US-7193039-B2
优先权日:1999-12-22
标题:Synthesis of a potent parmagnetic agonist (epm-3) of the melanocyte stimulating hormone containing amino acid-type stable free radical
发明人:NAKAIE CLOVIS RYUICHI; BARBOSA SIMONE DOS REIS; CILLI EDUARDO MAFFUD; LAMY-FREUND MARIA TEREZA; SIUITI ITO ARMANDO; VISCONTI MARIA APARECIDA; CASTRUCCI ANA MARIA DE LAURO
权利人:CONSELHO NACIONAL CNPQ
摘要:The present invention refers to the chemical synthesis and potentiality for application in several biochemical assays, of a potent agonist of the α-melanocyte stimulating hormone (α-MSH), labeled with an amino acid-type paramagnetic spin probe (Toac, or 2,2,6,6-tetramethylpiperidine-1-oxyl-amino-4-carboxylic acid), valuable for use in electron spin resonance and fluorescence allowing biochemical-clinical investigation of relevant physiological roles of α-MSH in animal organism. The referred analogue of the present invention, acetil-Toac 0 -(Nle 4 , DPhe 7 )-α-MSH, where (Nle 4 , DPhe 7 )-α-MSH is nominated commercially as Melanotanâ„¢ and although containing a non-natural compound in its structure such as Toac, maintained entirely its potent agonist potency. Its integral activity associated with the fact that it is naturally fluorescent (due to the Trp residue of its sequence) give to this labeled analogue a unique potential for a great variety of investigations regarding relevant physiological roles already known of this neuroimmuno-modulator.

专利号:US-6797829-B1
优先权日:1999-06-22
标 题 :Synthesis of a novel paramagnetic amino derivative (epm-5) for labelling chemical and biological macromolecules
发明人:NAKAIE CLOVIS RYUICHI; TOMINAGA MINEKO; DE MATTOS PAIVA ANTONIO CECHELLI; BARBOSA SIMONE DOS REIS; MARCHETTO REINALDO; SCHREIER SHIRLEY
权利人:CONSELHO NACIONAL CNPQ
摘要:The present invention refers to the synthesis and application of 2,2,5,5-tetramethylpyrrolidine-N-oxyl-(9-fluorenylmethyloxycarbonyl)-3-amine-4-carboxylic acid, a novel paramagnetic amino acid derivative (spin label), denominated Fmoc-Poac. Fmoc-Poac can be coupled to peptide sequences and other molecules or systems. It can be inserted anywhere in a peptide segment, even at an internal position if necessary, after removal of its temporary amine protecting group, Fmoc. Owing to its pyrrolidine structure, this molecule may induce differentiated conformations as compared with normal α-amino acids, thus being a valuable probe for structural-biological activity of several relevant peptides. The Poac-angiotensin II analogue was synthesized as a model according to its use as a chemical derivative.

专利号:US-12024498-B2
优先权日:2017-08-04
标 题 :Radical compounds and methods of using thereof
发明人:CONROY DANIEL W; JARONIEC CHRISTOPHER P
权利人:OHIO STATE INNOVATION FOUNDATION
摘要:Disclosed are methods for performing dynamic nuclear polarization using the polarizing agents described herein. In general, the methods involve (a) providing a frozen sample in a magnetic field, wherein the frozen sample includes a polarizing agent described herein and an analyte with at least one spin half nucleus; (b) polarizing the at least one spin half nucleus of the analyte by irradiating the frozen sample with radiation having a frequency that excites electron spin transitions in the polarizing agent; (c) optionally melting the sample to produce a molten sample; and (d) detecting nuclear spin transitions in the at least one spin half nucleus of the analyte in the frozen or molten sample. In certain embodiments, the polarizing agents can be peptide-based. In these embodiments, the polarizing agents can be readily prepared by solid-phase peptide synthesis.

专利号:US-2003212251-A1
优先权日:1999-12-22
标 题 :Synthesis of a potent parmagnetic agonist (epm-3) of the melanocyte stimulating hormone containing amino acid-type stable free radical

专利号:WO-0049867-A2
优先权日:1999-02-24
标 题 :Synthesis of the first paramagnetic and active analogue (epm-2) of the melanocyte stimulating hormone

专利号:EP-1204639-B1
优先权日:1999-06-22
标 题:Synthesis of a novel paramagnetic amino acid derivative (epm-5) for labelling chemical and biological macromolecules

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主要参考文献

[参考文献]: Cristina Peggion, Et Al. Total Syntheses In Solution Of Toac-Labelled Alamethicin F50/5 Analogues. Chem Biodivers. 2007 Jun;4(6):1183-99.
[参考文献]: Ethan S Karp, Et Al. Electron Paramagnetic Resonance Studies Of An Integral Membrane Peptide Inserted Into Aligned Phospholipid Bilayer Nanotube Arrays. J Am Chem Soc. 2006 Sep 20;128(37):12070-1.
[参考文献]: Harishchandra Ghimire, Et Al. Distance Measurements On A Dual-Labeled Toac Achr M2δ Peptide In Mechanically Aligned Dmpc Bilayers Via Dipolar Broadening Cw-Epr Spectroscopy. J Phys Chem B. 2012 Mar 29;116(12):3866-73.
[参考文献]: Harishchandra Ghimire, Et Al. Probing The Helical Tilt And Dynamic Properties Of Membrane-Bound Phospholamban In Magnetically Aligned Bicelles Using Electron Paramagnetic Resonance Spectroscopy. Biochim Biophys Acta. 2012 Mar;1818(3):645-50.
[参考文献]: Lars Thomas, Et Al. Membrane Interaction Of Neuropeptide Y Detected By Epr And Nmr Spectroscopy. Biochim Biophys Acta. 2005 Aug 15;1714(2):103-13.

合成参考文献


参考文献:10.1002/psc.1413
摘要:Gobbo M, Merli E, Biondi B, Oancea S, Toffoletti A, Formaggio F, Toniolo C. Synthesis and preliminary conformational analysis of TOAC spin‐labeled analogues of the medium‐length peptaibiotic tylopeptin B. Journal of Peptide Science. 2011 Nov 02;18(1):37–44. doi: 10.1002/psc.1413.
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