Thioguanine (BioDeep_00000001876)

 

Secondary id: BioDeep_00000408975

human metabolite Endogenous blood metabolite Chemicals and Drugs Cytotoxicity Volatile Flavor Compounds


代谢物信息卡片


2-Amino-1,7-dihydro-6H-purine-6-thione

化学式: C5H5N5S (167.026565)
中文名称: 硫鸟嘌呤
谱图信息: 最多检出来源 Homo sapiens(blood) 1.53%

分子结构信息

SMILES: C1=NC2=C(N1)C(=S)N=C(N2)N
InChI: InChI=1S/C5H5N5S/c6-5-9-3-2(4(11)10-5)7-1-8-3/h1H,(H4,6,7,8,9,10,11)

描述信息

Thioguanine is only found in individuals that have used or taken this drug. It is an antineoplastic compound which also has antimetabolite action. The drug is used in the therapy of acute leukemia. [PubChem]Thioguanine competes with hypoxanthine and guanine for the enzyme hypoxanthine-guanine phosphoribosyltransferase (HGPRTase) and is itself converted to 6-thioguanilyic acid (TGMP), which reaches high intracellular concentrations at therapeutic doses. TGMP interferes with the synthesis of guanine nucleotides by its inhibition of purine biosynthesis by pseudofeedback inhibition of glutamine-5-phosphoribosylpyrophosphate amidotransferase, the first enzyme unique to the de novo pathway of purine ribonucleotide synthesis. TGMP also inhibits the conversion of inosinic acid (IMP) to xanthylic acid (XMP) by competition for the enzyme IMP dehydrogenase. Thioguanine nucleotides are incorporated into both the DNA and the RNA by phosphodiester linkages, and some studies have shown that incorporation of such false bases contributes to the cytotoxicity of thioguanine. Its tumor inhibitory properties may be due to one or more of its effects on feedback inhibition of de novo purine synthesis; inhibition of purine nucleotide interconversions; or incorporation into the DNA and RNA. The overall result of its action is a sequential blockade of the utilization and synthesis of the purine nucleotides.
CONFIDENCE standard compound; INTERNAL_ID 640; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 1594; ORIGINAL_PRECURSOR_SCAN_NO 1590
CONFIDENCE standard compound; INTERNAL_ID 640; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 1575; ORIGINAL_PRECURSOR_SCAN_NO 1574
CONFIDENCE standard compound; INTERNAL_ID 640; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 1573; ORIGINAL_PRECURSOR_SCAN_NO 1568
CONFIDENCE standard compound; INTERNAL_ID 640; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 1582; ORIGINAL_PRECURSOR_SCAN_NO 1581
CONFIDENCE standard compound; INTERNAL_ID 640; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 1583; ORIGINAL_PRECURSOR_SCAN_NO 1581
CONFIDENCE standard compound; INTERNAL_ID 640; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 1576; ORIGINAL_PRECURSOR_SCAN_NO 1575
CONFIDENCE standard compound; INTERNAL_ID 640; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 855; ORIGINAL_PRECURSOR_SCAN_NO 852
CONFIDENCE standard compound; INTERNAL_ID 640; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 853; ORIGINAL_PRECURSOR_SCAN_NO 850
CONFIDENCE standard compound; INTERNAL_ID 640; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 852; ORIGINAL_PRECURSOR_SCAN_NO 850
CONFIDENCE standard compound; INTERNAL_ID 640; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 872; ORIGINAL_PRECURSOR_SCAN_NO 869
CONFIDENCE standard compound; INTERNAL_ID 640; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 865; ORIGINAL_PRECURSOR_SCAN_NO 862
CONFIDENCE standard compound; INTERNAL_ID 640; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 863; ORIGINAL_PRECURSOR_SCAN_NO 861
L - Antineoplastic and immunomodulating agents > L01 - Antineoplastic agents > L01B - Antimetabolites > L01BB - Purine analogues
C274 - Antineoplastic Agent > C186664 - Cytotoxic Chemotherapeutic Agent > C272 - Antimetabolite
C471 - Enzyme Inhibitor > C2254 - Amidophosphoribosyltransferase Inhibitor
D009676 - Noxae > D000963 - Antimetabolites
D000970 - Antineoplastic Agents
6-Thioguanine (Thioguanine; 2-Amino-6-purinethiol) is an anti-leukemia and immunosuppressant agent, acts as an inhibitor of SARS and MERS coronavirus papain-like proteases (PLpros) and also potently inhibits USP2 activity, with IC50s of 25 μM and 40 μM for Plpros and recombinant human USP2, respectively.

同义名列表

41 个代谢物同义名

2-Amino-1,7-dihydro-6H-purine-6-thione; 2-amino-6,7-dihydro-3H-purine-6-thione; GlaxoSmithKline brand OF thioguanine; GlaxoSmithKline brand OF tioguanine; Glaxo wellcome brand OF thioguanine; 2-Amino-1,9-dihydropurine-6-thione; Glaxo wellcome brand OF tioguanine; Tioguanine glaxosmithkline brand; Wellcome brand OF thioguanine; Thioguanine monosodium salt; 2-Aminopurine-6(1H)-thione; 6-Mercapto-2-aminopurine; 2-Amino-6-mercaptopurine; 2-Amino-6-merkaptopurin; Thioguanine hemihydrate; Anhydrous, thioguanine; Thioguanine anhydrous; 2-Aminopurine-6-thiol; 2-Amino-6-purinethiol; 2 Amino 6 purinethiol; 2-Aminopurin-6-thiol; Tioguanina wellcome; Thioguanine tabloid; 6-Mercaptoguanine; Thioguanin-GSK; Thioguanin GSK; 6 Thioguanine; ThioguaninGSK; 6-Thioguanine; Tioguaninum; thioguanine; 2-Amino 6MP; Tioguanina; Tioguanin; Tabloid; Lanvis; 6-TG; THG; TG; Thioguanine; Thioguanine



数据库引用编号

37 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

2 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(2)

PharmGKB(0)

3 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

  • PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。



文献列表

  • Qiang Zhang, Qiwei Liu, Ping He. Fully optimized new sensitive electrochemical device for the selective determination of 6-thioguanine anticancer drug in wastewater and biological samples. Chemosphere. 2023 Jul; 330(?):138634. doi: 10.1016/j.chemosphere.2023.138634. [PMID: 37030348]
  • Jinping Zhang, Meimei Gao, Ying Niu, Jiangang Sun. From DNMT1 degrader to ferroptosis promoter: Drug repositioning of 6-Thioguanine as a ferroptosis inducer in gastric cancer. Biochemical and biophysical research communications. 2022 05; 603(?):75-81. doi: 10.1016/j.bbrc.2022.03.026. [PMID: 35278883]
  • Wen Liu, Shana Zhou, Jing Liu, Xin Zhao, Zhe Feng, Dongmei Wang, Zhengjun Gong, Meikun Fan. Quantitative detection of 6-thioguanine in body fluids based on a free-standing liquid membrane SERS substrate. Analytical and bioanalytical chemistry. 2022 Feb; 414(4):1663-1670. doi: 10.1007/s00216-021-03790-x. [PMID: 34812902]
  • Pedro R Chocair, Precil Diego Miranda de Menezes Neves, Sara Mohrbacher, Maurilio Pacheco Neto, Victor A H Sato, Érico S Oliveira, Leonardo V Barbosa, Alessandra M Bales, Fagner Pereira da Silva, Américo L Cuvello-Neto, John A Duley. Case Report: Azathioprine: An Old and Wronged Immunosuppressant. Frontiers in immunology. 2022; 13(?):903012. doi: 10.3389/fimmu.2022.903012. [PMID: 35757730]
  • Martin Stanulla, Elke Schaeffeler, Anja Möricke, Swantje Buchmann, Martin Zimmermann, Svitlana Igel, Kjeld Schmiegelow, Christian Flotho, Hans Hartmann, Sabine Illsinger, Axel Sauerbrey, Stefanie V Junk, Peter Schütte, Laura Hinze, Melchior Lauten, Simon Modlich, Reinhard Kolb, Claudia Rossig, Georg Schwabe, Astrid K Gnekow, Gudrun Fleischhack, Paul Gerhard Schlegel, Holger J Schünemann, Christian P Kratz, Gunnar Cario, Martin Schrappe, Matthias Schwab. Hepatic sinusoidal obstruction syndrome and short-term application of 6-thioguanine in pediatric acute lymphoblastic leukemia. Leukemia. 2021 09; 35(9):2650-2657. doi: 10.1038/s41375-021-01203-7. [PMID: 33714975]
  • I T Gatchell, R B Huntley, N P Schultes, G S Mourad. The guanine-hypoxanthine permease GhxP of Erwinia amylovora facilitates the influx of the toxic guanine derivative 6-thioguanine. Journal of applied microbiology. 2021 Jun; 130(6):2018-2028. doi: 10.1111/jam.14925. [PMID: 33152175]
  • Leandro Rocha Silva, Paulo Fernando da Silva Santos-Júnior, Júlia de Andrade Brandão, Letícia Anderson, Ênio José Bassi, João Xavier de Araújo-Júnior, Sílvia Helena Cardoso, Edeildo Ferreira da Silva-Júnior. Druggable targets from coronaviruses for designing new antiviral drugs. Bioorganic & medicinal chemistry. 2020 11; 28(22):115745. doi: 10.1016/j.bmc.2020.115745. [PMID: 33007557]
  • Rafael Martín-Masot, María Pilar Ortiz Pérez, Natalia Ramos Rueda, Juliana Serrano Nieto, Javier Blasco-Alonso, Víctor Manuel Navas-López. [Laboratory determination of thiopurine levels in paediatric patients with inflammatory bowel disease]. Anales de pediatria. 2020 Jul; 93(1):34-40. doi: 10.1016/j.anpedi.2019.10.005. [PMID: 31784325]
  • Sandra Bohn Thomsen, Kristine Højgaard Allin, Johan Burisch, Camilla Bjørn Jensen, Susanne Hansen, Lise Lotte Gluud, Klaus Theede, Marianne Kiszka-Kanowitz, Anette Mertz Nielsen, Tine Jess. Outcome of concomitant treatment with thiopurines and allopurinol in patients with inflammatory bowel disease: A nationwide Danish cohort study. United European gastroenterology journal. 2020 02; 8(1):68-76. doi: 10.1177/2050640619868387. [PMID: 32213059]
  • Jiaqi Han, Shenghui Mei, Jiamin Xu, Dongjie Zhang, Siyao Jin, Zhigang Zhao, Libo Zhao. Simultaneous UPLC-MS/MS Determination of 6-mercaptopurine, 6-methylmercaptopurine and 6-thioguanine in Plasma: Application to the Pharmacokinetic Evaluation of Novel Dosage forms in Beagle Dogs. Current pharmaceutical design. 2020; 26(46):6013-6020. doi: 10.2174/1381612826999200820161343. [PMID: 32867649]
  • Shabi Abbas Zaidi. Effective imprinting of an anticancer drug, 6-thioguanine, via mussel-inspired self-polymerization of dopamine over reduced graphene oxide. The Analyst. 2019 Mar; 144(7):2345-2352. doi: 10.1039/c8an02348d. [PMID: 30785148]
  • Mohammad Amjadi, Tooba Hallaj, Rana Salari. A sensitive colorimetric probe for detection of 6-thioguanine based on its protective effect on the silver nanoprisms. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy. 2019 Mar; 210(?):30-35. doi: 10.1016/j.saa.2018.11.002. [PMID: 30428429]
  • Dharamveer Basude, Lucy Bates, Gemma Sheldon, Siba P Paul. Availability of lab-based investigations for children with inflammatory bowel disease. British journal of hospital medicine (London, England : 2005). 2019 Jan; 80(1):56. doi: 10.12968/hmed.2019.80.1.56. [PMID: 30592670]
  • Anne Grosen, Jacob Nersting, Mona Bungum, Lisbet Ambrosius Christensen, Kjeld Schmiegelow, Marcello Spanò, Mette Julsgaard, Eugenia Cordelli, Giorgio Leter, Peter Braad Larsen, Christian Lodberg Hvas, Jens Kelsen. Sperm DNA Integrity is Unaffected by Thiopurine Treatment in Men With Inflammatory Bowel Disease. Journal of Crohn's & colitis. 2019 Jan; 13(1):3-11. doi: 10.1093/ecco-jcc/jjy086. [PMID: 29917107]
  • Floris F van den Brand, Carin M J van Nieuwkerk, Bart J Verwer, Ynto S de Boer, Nanne K H de Boer, Chris J J Mulder, Elisabeth Bloemena, Christine M Bakker, Jan M Vrolijk, Joost P H Drenth, Adriaan C I T L Tan, Frank Ter Borg, Martijn J Ter Borg, Sven J van den Hazel, Akin Inderson, Maarten E Tushuizen, Gerd Bouma. Biochemical efficacy of tioguanine in autoimmune hepatitis: a retrospective review of practice in the Netherlands. Alimentary pharmacology & therapeutics. 2018 10; 48(7):761-767. doi: 10.1111/apt.14939. [PMID: 30109891]
  • Sandra Bohn Thomsen, Marianne Kiszka-Kanowitz, Klaus Theede, Lise Lotte Gluud, Anette Mertz Nielsen. Optimized thiopurine therapy before withdrawal of anti-tumour necrosis factor-α in patients with Crohn's disease. European journal of gastroenterology & hepatology. 2018 10; 30(10):1155-1158. doi: 10.1097/meg.0000000000001194. [PMID: 29975242]
  • Agnieszka Litomska, Keishi Ishida, Kyle L Dunbar, Marco Boettger, Sébastien Coyne, Christian Hertweck. Enzymatic Thioamide Formation in a Bacterial Antimetabolite Pathway. Angewandte Chemie (International ed. in English). 2018 09; 57(36):11574-11578. doi: 10.1002/anie.201804158. [PMID: 29947149]
  • Byung Kwan Park. Low-dose CT protocols for guiding radiofrequency ablation for the treatment of small renal cell carcinomas. International journal of hyperthermia : the official journal of European Society for Hyperthermic Oncology, North American Hyperthermia Group. 2018 09; 34(6):877-882. doi: 10.1080/02656736.2017.1373408. [PMID: 28847190]
  • Xin-Yu Zhang, Adnan A Elfarra. Toxicity mechanism-based prodrugs: glutathione-dependent bioactivation as a strategy for anticancer prodrug design. Expert opinion on drug discovery. 2018 09; 13(9):815-824. doi: 10.1080/17460441.2018.1508207. [PMID: 30101640]
  • Blanka Stiburkova, Katerina Pavelcova, Lenka Petru, Jakub Krijt. Thiopurine-induced toxicity is associated with dysfunction variant of the human molybdenum cofactor sulfurase gene (xanthinuria type II). Toxicology and applied pharmacology. 2018 08; 353(?):102-108. doi: 10.1016/j.taap.2018.06.015. [PMID: 29935280]
  • Olivia A Attallah, Medhat A Al-Ghobashy, Ahmed Taha Ayoub, Marianne Nebsen. Magnetic molecularly imprinted polymer nanoparticles for simultaneous extraction and determination of 6-mercaptopurine and its active metabolite thioguanine in human plasma. Journal of chromatography. A. 2018 Aug; 1561(?):28-38. doi: 10.1016/j.chroma.2018.05.038. [PMID: 29798806]
  • Stefano Lazzarano, Marek Kučka, João P L Castro, Ronald Naumann, Paloma Medina, Michael N C Fletcher, Rebecka Wombacher, Joost Gribnau, Tino Hochepied, Marc Van Montagu, Claude Libert, Yingguang Frank Chan. Genetic mapping of species differences via in vitro crosses in mouse embryonic stem cells. Proceedings of the National Academy of Sciences of the United States of America. 2018 04; 115(14):3680-3685. doi: 10.1073/pnas.1717474115. [PMID: 29563231]
  • Hongyan Zeng, Li Li, Yaping Ding, Qi Zhuang. Simple and selective determination of 6-thioguanine by using polyethylenimine (PEI) functionalized carbon dots. Talanta. 2018 Feb; 178(?):879-885. doi: 10.1016/j.talanta.2017.09.087. [PMID: 29136909]
  • Mohammad Amjadi, Roghayeh Shokri, Tooba Hallaj. Interaction of glucose-derived carbon quantum dots with silver and gold nanoparticles and its application for the fluorescence detection of 6-thioguanine. Luminescence : the journal of biological and chemical luminescence. 2017 May; 32(3):292-297. doi: 10.1002/bio.3177. [PMID: 27406471]
  • Hassan Karimi-Maleh, Abdollah Fallah Shojaei, Khalil Tabatabaeian, Fatemeh Karimi, Shahryar Shakeri, Reza Moradi. Simultaneous determination of 6-mercaptopruine, 6-thioguanine and dasatinib as three important anticancer drugs using nanostructure voltammetric sensor employing Pt/MWCNTs and 1-butyl-3-methylimidazolium hexafluoro phosphate. Biosensors & bioelectronics. 2016 Dec; 86(?):879-884. doi: 10.1016/j.bios.2016.07.086. [PMID: 27494812]
  • Medhat A Al-Ghobashy, Said A Hassan, Doaa H Abdelaziz, Noha M Elhosseiny, Nirmeen A Sabry, Ahmed S Attia, Manal H El-Sayed. Development and validation of LC-MS/MS assay for the simultaneous determination of methotrexate, 6-mercaptopurine and its active metabolite 6-thioguanine in plasma of children with acute lymphoblastic leukemia: Correlation with genetic polymorphism. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2016 Dec; 1038(?):88-94. doi: 10.1016/j.jchromb.2016.10.035. [PMID: 27802917]
  • Hadi Beitollahi, Susan Ghofrani Ivari, Masoud Torkzadeh-Mahani. Voltammetric determination of 6-thioguanine and folic acid using a carbon paste electrode modified with ZnO-CuO nanoplates and modifier. Materials science & engineering. C, Materials for biological applications. 2016 Dec; 69(?):128-33. doi: 10.1016/j.msec.2016.06.064. [PMID: 27612697]
  • Mohd Ishtikhar, Anam Khan, Chih-Kai Chang, Lilian Tsai-Wei Lin, Steven S-S Wang, Rizwan Hasan Khan. Effect of guanidine hydrochloride and urea on the interaction of 6-thioguanine with human serum albumin: a spectroscopic and molecular dynamics based study. Journal of biomolecular structure & dynamics. 2016 Jul; 34(7):1409-20. doi: 10.1080/07391102.2015.1054433. [PMID: 26208966]
  • D Zochowska, J Zegarska, E Hryniewiecka, E Samborowska, R Jazwiec, W Tszyrsznic, A Borowiec, M Dadlez, L Paczek. Determination of Concentrations of Azathioprine Metabolites 6-Thioguanine and 6-Methylmercaptopurine in Whole Blood With the Use of Liquid Chromatography Combined With Mass Spectrometry. Transplantation proceedings. 2016 Jun; 48(5):1836-9. doi: 10.1016/j.transproceed.2016.01.084. [PMID: 27496503]
  • Pramod Katara, Himani Kuntal. TPMT Polymorphism: When Shield Becomes Weakness. Interdisciplinary sciences, computational life sciences. 2016 Jun; 8(2):150-155. doi: 10.1007/s12539-015-0111-1. [PMID: 26297310]
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  • Mohammad Amjadi, Leila Farzampour. Selective turn-on fluorescence assay of 6-thioguanine by using harmine-modified silver nanoparticles. Luminescence : the journal of biological and chemical luminescence. 2014 Sep; 29(6):689-94. doi: 10.1002/bio.2612. [PMID: 24288350]
  • A Wensing, M Gernold, S Jock, R Jansen, K Geider. Identification and genetics of 6-thioguanine secreted by Erwinia species and its interference with the growth of other bacteria. Molecular genetics and genomics : MGG. 2014 Apr; 289(2):215-23. doi: 10.1007/s00438-013-0805-1. [PMID: 24374865]
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  • Sébastien Coyne, Cornelia Chizzali, Mohammed N A Khalil, Agnieszka Litomska, Klaus Richter, Ludger Beerhues, Christian Hertweck. Biosynthesis of the antimetabolite 6-thioguanine in Erwinia amylovora plays a key role in fire blight pathogenesis. Angewandte Chemie (International ed. in English). 2013 Sep; 52(40):10564-8. doi: 10.1002/anie.201305595. [PMID: 24038828]
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