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Original Articles

New Photolabile Protecting Groups in Nucleoside and Nucleotide Chemistry—Synthesis, Cleavage Mechanisms and Applications

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Pages 1987-1996 | Published online: 22 Aug 2006

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D. Wöll, S. Walbert, K.-P. Stengele, R. Green, T. Albert, W. Pfleiderer & U. E. Steiner. (2003) More Efficient Photolithographic Synthesis of DNA-Chips by Photosensitization. Nucleosides, Nucleotides & Nucleic Acids 22:5-8, pages 1395-1398.
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Articles from other publishers (50)

Jincai Wang, Yingle Feng, Taotao Sun, Qi Zhang & Yonghai Chai. (2022) Photolabile 2-(2-Nitrophenyl)-propyloxycarbonyl (NPPOC) for Stereoselective Glycosylation and Its Application in Consecutive Assembly of Oligosaccharides. The Journal of Organic Chemistry 87:5, pages 3402-3421.
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Jory Lietard, Adrien Leger, Yaniv Erlich, Norah Sadowski, Winston Timp & Mark M Somoza. (2021) Chemical and photochemical error rates in light-directed synthesis of complex DNA libraries. Nucleic Acids Research 49:12, pages 6687-6701.
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Roy Weinstain, Tomáš Slanina, Dnyaneshwar Kand & Petr Klán. (2020) Visible-to-NIR-Light Activated Release: From Small Molecules to Nanomaterials. Chemical Reviews 120:24, pages 13135-13272.
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Yeonwoo Jeong, Dong Gyun Jwa, Ahrom You, Sora Park, Jeung Gon Kim, Sung Min Kang & Min Kim. (2019) Photochemical Control of Polydopamine Coating in an Aprotic Organic Solvent. Asian Journal of Organic Chemistry 8:9, pages 1610-1612.
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Nicolas Zivic, Paula K. Kuroishi, Frédéric Dumur, Didier Gigmes, Andrew P. Dove & Haritz Sardon. (2019) Recent Advances and Challenges in the Design of Organic Photoacid and Photobase Generators for Polymerizations. Angewandte Chemie International Edition 58:31, pages 10410-10422.
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Nicolas Zivic, Paula K. Kuroishi, Frédéric Dumur, Didier Gigmes, Andrew P. Dove & Haritz Sardon. (2019) Organische Photosäuren‐ und Photobasenbildner für Polymerisationen: Jüngste Fortschritte und Herausforderungen. Angewandte Chemie 131:31, pages 10518-10531.
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Enrico Faggi, Jordi Aguilera, Rubén Sáez, Ferran Pujol, Jordi Marquet, Jordi Hernando & Rosa María Sebastián. (2019) Wavelength-Tunable Light-Induced Polymerization of Cyanoacrylates Using Photogenerated Amines. Macromolecules 52:6, pages 2329-2339.
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Kathrin Hölz, Julia K. Hoi, Erika Schaudy, Veronika Somoza, Jory Lietard & Mark M. Somoza. (2018) High-Efficiency Reverse (5′→3′) Synthesis of Complex DNA Microarrays. Scientific Reports 8:1.
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Payam E. Farahani, Steven M. Adelmund, Jared A. Shadish & Cole A. DeForest. (2017) Photomediated oxime ligation as a bioorthogonal tool for spatiotemporally-controlled hydrogel formation and modification. Journal of Materials Chemistry B 5:23, pages 4435-4442.
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Matej Sack, Kathrin Hölz, Ann-Katrin Holik, Nicole Kretschy, Veronika Somoza, Klaus-Peter Stengele & Mark M. Somoza. (2016) Express photolithographic DNA microarray synthesis with optimized chemistry and high-efficiency photolabile groups. Journal of Nanobiotechnology 14:1.
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Richard A. Lawson & Alex P.G. Robinson. 2016. Materials and Processes for Next Generation Lithography. Materials and Processes for Next Generation Lithography 1 90 .
Nicole Kretschy, Ann‐Katrin Holik, Veronika Somoza, Klaus‐Peter Stengele & Mark M. Somoza. (2015) Next‐Generation o ‐Nitrobenzyl Photolabile Groups for Light‐Directed Chemistry and Microarray Synthesis . Angewandte Chemie International Edition 54:29, pages 8555-8559.
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Nicole Kretschy, Ann‐Katrin Holik, Veronika Somoza, Klaus‐Peter Stengele & Mark M. Somoza. (2015) o ‐Nitrobenzyl‐photolabile Gruppen der nächsten Generation in der lichtgesteuerten Chemie und der Synthese von Mikroarrays . Angewandte Chemie 127:29, pages 8675-8679.
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Gang Wang, Tao Peng, Shouguo Zhang, Junyi Wang, Xiaoxue Wen, Haiyan Yan, Liming HuLin Wang. (2015) 2-(2-Nitrophenyl) propyl: a rapidly released photolabile COOH-protecting group for solid-phase peptide synthesis. RSC Advances 5:36, pages 28344-28348.
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. 2014. Greene's Protective Groups in Organic Synthesis. Greene's Protective Groups in Organic Synthesis 17 471 .
Weixian Xi, Matthias Krieger, Christopher J. Kloxin & Christopher N. Bowman. (2013) A new photoclick reaction strategy: photo-induced catalysis of the thiol-Michael addition via a caged primary amine. Chem. Commun. 49:40, pages 4504-4506.
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Hui Zhao, Elizabeth S. Sterner, E. Bryan Coughlin & Patrick Theato. (2012) o -Nitrobenzyl Alcohol Derivatives: Opportunities in Polymer and Materials Science . Macromolecules 45:4, pages 1723-1736.
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Brian P. Stupi, Hong Li, Jinchun Wang, Weidong Wu, Sidney E. Morris, Vladislav A. Litosh, Jesse Muniz, Megan N. Hersh & Michael L. Metzker. (2012) Stereochemistry of Benzylic Carbon Substitution Coupled with Ring Modification of 2‐Nitrobenzyl Groups as Key Determinants for Fast‐Cleaving Reversible Terminators. Angewandte Chemie International Edition 51:7, pages 1724-1727.
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Brian P. Stupi, Hong Li, Jinchun Wang, Weidong Wu, Sidney E. Morris, Vladislav A. Litosh, Jesse Muniz, Megan N. Hersh & Michael L. Metzker. (2012) Stereochemischer Verlauf einer Benzyl‐Kohlenstoff‐Substitution kombiniert mit Ringmodifikation der 2‐Nitrobenzylgruppen als Schlüsselfaktoren für schnell spaltende, reversible Terminatoren. Angewandte Chemie 124:7, pages 1756-1759.
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Marcin K. Chmielewski, Ewa Tykarska, Wojciech T. Markiewicz & Wojciech Rypniewski. (2012) Engineering N-(2-pyridyl)aminoethyl alcohols as potential precursors of thermolabile protecting groups. New J. Chem. 36:3, pages 603-612.
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Arcan Güven, Tamara Dworeck, Marco Fioroni & Ulrich Schwaneberg. (2011) Residue K556-A Light Triggerable Gatekeeper to Sterically Control Translocation in FhuA. Advanced Engineering Materials 13:9, pages B324-B329.
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Michael C. Pirrung, Biswajit Gopal Roy & Surendra Gadamsetty. (2010) Structure-reactivity relationships in (2-hydroxyethyl)benzophenone photoremovable protecting Groups. Tetrahedron 66:17, pages 3147-3151.
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Ji-Yen Cheng & Huai-Yi Chen. (2009) Microfluidic ARray Synthesizer (MArS) for rapid preparation and hybridization of custom DNA microarray. Biotechnology and Bioengineering 104:2, pages 400-407.
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Katja Drexler, Julia Smirnova, Marina Galetskaya, Sönke Voss, Mikhail Fonin, Johannes Boneberg, Ulrich Rüdiger, Paul Leiderer & Ulrich E. Steiner. (2009) X-ray Photoelectron Spectroscopy- and Surface Plasmon Resonance-Detected Photo Release of Photolabile Protecting Groups from Nucleoside Self-Assembled Monolayers on Gold Surfaces. Langmuir 25:18, pages 10794-10801.
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Hua Yi, Stéphane Maisonneuve & Juan Xie. (2009) Synthesis, glycosylation and photolysis of photolabile 2-(2-nitrophenyl)propyloxycarbonyl (NPPOC) protected glycopyranosides. Organic & Biomolecular Chemistry 7:18, pages 3847.
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Dominik Wöll, Julia Smirnova, Marina Galetskaya, Tamara Prykota, Jochen Bühler, Klaus‐Peter Stengele, Wolfgang Pfleiderer & Ulrich E. Steiner. (2008) Intramolecular Sensitization of Photocleavage of the Photolabile 2‐(2‐Nitrophenyl)propoxycarbonyl (NPPOC) Protecting Group: Photoproducts and Photokinetics of the Release of Nucleosides. Chemistry – A European Journal 14:21, pages 6490-6497.
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Dominik Wöll, Stefan Laimgruber, Marina Galetskaya, Julia Smirnova, Wolfgang Pfleiderer, Björn Heinz, Peter Gilch & Ulrich E. Steiner. (2007) On the Mechanism of Intramolecular Sensitization of Photocleavage of the 2-(2-Nitrophenyl)propoxycarbonyl (NPPOC) Protecting Group. Journal of the American Chemical Society 129:40, pages 12148-12158.
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Andrea Giordano, Sirus Zarbakhsh & Carsten Schultz. 2007. Chemical Biology. Chemical Biology 140 173 .
Shane T. Flickinger, Madhusudan Patel, Brock F. Binkowski, Aaron M. Lowe, Mo-Huang Li, Changhan Kim, Franco Cerrina & Peter J. Belshaw. (2006) Spatial Photorelease of Oligonucleotides, Using a Safety-Catch Photolabile Linker. Organic Letters 8:11, pages 2357-2360.
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Dominik Wöll, Julia Smirnova, Wolfgang Pfleiderer & Ulrich E. Steiner. (2006) Highly Efficient Photolabile Protecting Groups with Intramolecular Energy Transfer. Angewandte Chemie International Edition 45:18, pages 2975-2978.
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Dominik Wöll, Julia Smirnova, Wolfgang Pfleiderer & Ulrich E. Steiner. (2006) Hocheffiziente photolabile Schutzgruppen mit intramolekularem Energietransfer. Angewandte Chemie 118:18, pages 3042-3045.
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Joulia Smirnova, Dominik Wöll, Wolfgang Pfleiderer & Ulrich E. Steiner. (2005) Synthesis of Caged Nucleosides with Photoremovable Protecting Groups Linked to Intramolecular Antennae. Helvetica Chimica Acta 88:4, pages 891-904.
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Markus Beier & Jörg D. Hoheisel. (2005) DNA Microarray Preparation by Light‐Controlled In Situ Synthesis. Current Protocols in Nucleic Acid Chemistry 20:1.
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George Papageorgiou, Andreas Barth & John E. T. Corrie. (2005) Flash photolytic release of alcohols from photolabile carbamates or carbonates is rate-limited by decarboxylation of the photoproduct. Photochemical & Photobiological Sciences 4:2, pages 216-220.
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Lenz Kröck & Alexander Heckel. (2005) Photoinduced Transcription by Using Temporarily Mismatched Caged Oligonucleotides. Angewandte Chemie International Edition 44:3, pages 471-473.
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Lenz Kröck & Alexander Heckel. (2005) Lichtinduzierte Transkription mit vorübergehend fehlgepaarten Oligonucleotiden. Angewandte Chemie 117:3, pages 475-477.
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I. Shcherbakova & A.F. Pozharskii. 2005. Comprehensive Organic Functional Group Transformations II. Comprehensive Organic Functional Group Transformations II 89 235 .
Vicente Marchán, Jacek Cieślak, Victor Livengood & Serge L. Beaucage. (2004) 2,2,5,5-Tetramethylpyrrolidin-3-one-1-sulfinyl Group for 5‘-Hydroxyl Protection of Deoxyribonucleoside Phosphoramidites in the Solid-Phase Preparation of DNA Oligonucleotides. Journal of the American Chemical Society 126:31, pages 9601-9610.
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Ichiro Suzuki, Shinsaku Uno, Yuko Tsuchiya, Akira Shigenaga, Hisao Nemoto & Masayuki Shibuya. (2004) Synthesis and DNA damaging ability of enediyne model compounds possessing photo-triggering devices. Bioorganic & Medicinal Chemistry Letters 14:11, pages 2959-2962.
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Markus Beier & Jörg D. Hoheisel. (2004) Synthesis of 5′‐ O ‐Phosphoramidites with a Photolabile 3′‐ O ‐Protecting Group . Current Protocols in Nucleic Acid Chemistry 17:1.
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Xiaolian Gao, Erdogan Gulari & Xiaochuan Zhou. (2004) In situ synthesis of oligonucleotide microarrays. Biopolymers 73:5, pages 579-596.
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Sigrid Bühler, Irene Lagoja, Heiner Giegrich, Klaus‐Peter Stengele & Wolfgang Pfleiderer. (2004) New Types of Very Efficient Photolabile Protecting Groups Based upon the [2‐(2‐Nitrophenyl)propoxy]carbonyl (NPPOC) Moiety. Helvetica Chimica Acta 87:3, pages 620-659.
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Marcin K. ChmielewskiVicente MarchánJacek CieślakAndrzej GrajkowskiVictor LivengoodUrsula MünchAndrzej WilkSerge L. Beaucage. (2003) Thermolytic Carbonates for Potential 5‘-Hydroxyl Protection of Deoxyribonucleosides. The Journal of Organic Chemistry 68:26, pages 10003-10012.
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Abraham Yousef, Jong-Ill Lee, Ii, Peter Conrad & Richard Givens. 2003. CRC Handbookof Organic Photochemistry and Photobiology, Volumes 1 & 2, Second Edition. CRC Handbookof Organic Photochemistry and Photobiology, Volumes 1 & 2, Second Edition.
Michael P. Coleman & Mary K. Boyd. (2002) S-Pixyl Analogues as Photocleavable Protecting Groups for Nucleosides. The Journal of Organic Chemistry 67:22, pages 7641-7648.
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Serge L. Beaucage. 2001. Encyclopedia of Reagents for Organic Synthesis. Encyclopedia of Reagents for Organic Synthesis.
Michael J. Heller. (2002) DNA Microarray Technology: Devices, Systems, and Applications. Annual Review of Biomedical Engineering 4:1, pages 129-153.
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Anna Paola Pelliccioli & Jakob Wirz. (2002) Photoremovable protecting groups: reaction mechanisms and applications. Photochemical & Photobiological Sciences 1:7, pages 441-458.
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Michael C. Pirrung, Laixin Wang & Michael P. Montague-Smith. (2001) 3‘-Nitrophenylpropyloxycarbonyl (NPPOC) Protecting Groups for High-Fidelity Automated 5‘ → 3‘ Photochemical DNA Synthesis. Organic Letters 3:8, pages 1105-1108.
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H. GIEGRICH, S. EISELE‐BUEHLER, CH. HERMANN, E. KVASYAK, R. CHARUBALA & W. PFLEIDERER. (2010) ChemInform Abstract: New Photolabile Protecting Groups in Nucleoside and Nucleotide Chemistry — Synthesis, Cleavage Mechanisms and Applications.. ChemInform 30:5.
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