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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 26, 1996 - Issue 17
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Original Articles

A Two Step Synthesis of the Nucleoside Q Precursor 2-Amino-5-cyanopyrrolo[2,3-d]pyrimidin 4-one (PreQo)

Michael T. Migawa Department of Chemistry, College of Literature, Science, and Arts, Ann Arbor, Michigan, 48109-1065; Department of Medicinal Chemistry, College of Pharmacy; The University of Michigan, Ann Arbor, Michigan, 48109-1065
,
Jack M. Hinkley Department of Chemistry, College of Literature, Science, and Arts, Ann Arbor, Michigan, 48109-1065; Department of Medicinal Chemistry, College of Pharmacy; The University of Michigan, Ann Arbor, Michigan, 48109-1065
,
Geoffrey C. Hoops Department of Chemistry, College of Literature, Science, and Arts, Ann Arbor, Michigan, 48109-1065; Department of Medicinal Chemistry, College of Pharmacy; The University of Michigan, Ann Arbor, Michigan, 48109-1065
&
Leroy B. Townsend Department of Chemistry, College of Literature, Science, and Arts, Ann Arbor, Michigan, 48109-1065; Department of Medicinal Chemistry, College of Pharmacy; The University of Michigan, Ann Arbor, Michigan, 48109-1065
Pages 3317-3322 | Received 22 Mar 1996, Published online: 21 Aug 2006

Citations (25)

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Xiaojing Wang, Punit P. Seth, Ray Ranken, Eric E. Swayze & Michael T. Migawa. (2004) Synthesis and Biological Activity of 5‐Fluorotubercidin . Nucleosides, Nucleotides & Nucleic Acids 23:1-2, pages 161-170.
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Articles from other publishers (24)

Samanthi Herath Gedara, Evan Wood, Andrew Gustafson, Cui Liang, Shr-Hau Hung, Joshua Savage, Phuc Phan, Amit Luthra, Valérie de Crécy-Lagard, Peter Dedon, Manal A Swairjo & Dirk Iwata-Reuyl. (2023) 7-Deazaguanines in DNA: functional and structural elucidation of a DNA modification system. Nucleic Acids Research 51:8, pages 3836-3854.
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Maurice Sebastiani, Christina Behrens, Stefanie Dörr, Hans-Dieter Gerber, Rania Benazza, Oscar Hernandez-Alba, Sarah Cianférani, Gerhard Klebe, Andreas Heine & Klaus Reuter. (2022) Structural and Biochemical Investigation of the Heterodimeric Murine tRNA-Guanine Transglycosylase. ACS Chemical Biology 17:8, pages 2229-2247.
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Alexis J. A. Hennessy, Wenli Huang, Chloé Savary & Dominic J. Campopiano. (2021) Creation of an Engineered Amide Synthetase Biocatalyst by the Rational Separation of a Two‐Step Nitrile Synthetase. ChemBioChem 23:4.
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Allen F. Brooks, George A. Garcia & Hollis D. Showalter. (2021) Synthesis of azide congeners of preQ 1 as potential substrates for tRNA guanine transglycosylase . Journal of Heterocyclic Chemistry 58:5, pages 1192-1198.
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Ben Turner, Brett W. Burkhart, Katrin Weidenbach, Robert Ross, Patrick A. Limbach, Ruth A. Schmitz, Valérie de Crécy-Lagard, Kenneth M. Stedman, Thomas J. Santangelo & Dirk Iwata-Reuyl. (2020) Archaeosine Modification of Archaeal tRNA: Role in Structural Stabilization. Journal of Bacteriology 202:8.
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Natsuhisa Oka, Akane Fukuta & Kaori Ando. (2018) A practical synthesis of archaeosine and its base. Tetrahedron 74:39, pages 5709-5714.
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Birgit Wilding, Stefan Faschauner & Norbert Klempier. (2015) A practical synthesis of 5-functionalized thieno[2,3-d]pyrimidines. Tetrahedron Letters 56:30, pages 4486-4489.
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Sabin Llona-Minguez & Simon P Mackay. (2014) Stereoselective synthesis of carbocyclic analogues of the nucleoside Q precursor (PreQ 0 ) . Beilstein Journal of Organic Chemistry 10, pages 1333-1338.
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Yuichiro Nomura, Yumiko Onda, Satoshi Ohno, Hiroki Taniguchi, Kaori Ando, Natsuhisa Oka, Kazuya Nishikawa & Takashi Yokogawa. (2013) Purification and comparison of native and recombinant tRNA-guanine transglycosylases from Methanosarcina acetivorans. Protein Expression and Purification 88:1, pages 13-19.
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Kathrin Moeller, Giang-Son Nguyen, Frank Hollmann & Ulf Hanefeld. (2013) Expression and characterization of the nitrile reductase queF from E. coli. Enzyme and Microbial Technology 52:3, pages 129-133.
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Yi-Chen Chen, Allen F. Brooks, DeeAnne M. Goodenough-Lashua, Jeffrey D. Kittendorf, Hollis D. Showalter & George A. Garcia. (2011) Evolution of eukaryal tRNA-guanine transglycosylase: insight gained from the heterocyclic substrate recognition by the wild-type and mutant human and Escherichia coli tRNA-guanine transglycosylases. Nucleic Acids Research 39:7, pages 2834-2844.
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Allen F. Brooks, George A. Garcia & H.D. Hollis Showalter. (2010) A short, concise synthesis of queuine. Tetrahedron Letters 51:32, pages 4163-4165.
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Anjanette J. Turbiak, Jeff W. Kampf & H.D. Hollis Showalter. (2010) A novel synthesis of 3-(substituted)pyrimido[4,5-c]pyridazine-5,7(1H,6H)-diones. Tetrahedron Letters 51:9, pages 1326-1328.
Crossref
Süreyya Ölgen, Yasemin G Isgör & Tülay Çoban. (2008) Synthesis and Activity of Novel 5‐Substituted Pyrrolo[2,3‐ d ]pyrimidine Analogues as pp60 c‐Src Tyrosine Kinase Inhibitors . Archiv der Pharmazie 341:2, pages 113-120.
Crossref
T.J. Delia. 2008. Comprehensive Heterocyclic Chemistry III. Comprehensive Heterocyclic Chemistry III 339 430 .
Davide Quaranta, Reid McCarty, Vahe Bandarian & Christopher Rensing. (2007) The Copper-Inducible cin Operon Encodes an Unusual Methionine-Rich Azurin-Like Protein and a Pre-Q 0 Reductase in Pseudomonas putida KT2440 . Journal of Bacteriology 189:14, pages 5361-5371.
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Adam Roth, Wade C Winkler, Elizabeth E Regulski, Bobby W K Lee, Jinsoo Lim, Inbal Jona, Jeffrey E Barrick, Ankita Ritwik, Jane N Kim, Rüdiger Welz, Dirk Iwata-Reuyl & Ronald R Breaker. (2007) A riboswitch selective for the queuosine precursor preQ1 contains an unusually small aptamer domain. Nature Structural & Molecular Biology 14:4, pages 308-317.
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Tobias Brückl, Florian Klepper, Katrin Gutsmiedl & Thomas Carell. (2007) A short and efficient synthesis of the tRNA nucleosides PreQ0 and archaeosine. Organic & Biomolecular Chemistry 5:23, pages 3821.
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Florian Klepper, Kurt Polborn & Thomas Carell. (2005) Robust Synthesis and Crystal‐Structure Analysis of 7‐Cyano‐7‐deazaguanine (PreQ 0 Base) and 7‐(Aminomethyl)‐7‐deazaguanine (PreQ 1 Base) . Helvetica Chimica Acta 88:10, pages 2610-2616.
Crossref
Steven G. Van Lanen, John S. Reader, Manal A. Swairjo, Valérie de Crécy-Lagard, Bobby Lee & Dirk Iwata-Reuyl. (2005) From cyclohydrolase to oxidoreductase: Discovery of nitrile reductase activity in a common fold. Proceedings of the National Academy of Sciences 102:12, pages 4264-4269.
Crossref
Ruth Brenk, Milton T. Stubbs, Andreas Heine, Klaus Reuter & Gerhard Klebe. (2003) Flexible Adaptations in the Structure of the tRNA-Modifying Enzyme tRNA-Guanine Transglycosylase and Their Implications for Substrate Selectivity, Reaction Mechanism and Structure-Based Drug Design. ChemBioChem 4:10, pages 1066-1077.
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Charles J. Barnett & Lana M. Grubb. (2000) Total Synthesis of Q Base (Queuine). Tetrahedron 56:47, pages 9221-9225.
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Ying Bai, David T. Fox, Judy A. Lacy, Steven G. Van Lanen & Dirk Iwata-Reuyl. (2000) Hypermodification of tRNA in Thermophilic Archaea. Journal of Biological Chemistry 275:37, pages 28731-28738.
Crossref
M. T. MIGAWA, J. M. HINKLEY, G. C. HOOPS & L. B. TOWNSEND. (2010) ChemInform Abstract: Two Step Synthesis of the Nucleoside Q Precursor 2‐Amino‐5‐ cyanopyrrolo(2,3‐d)pyrimidin‐4‐one (PreQ0).. ChemInform 27:48.
Crossref

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