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Collect. Czech. Chem. Commun. 1993, 58, S170-S173
https://doi.org/10.1135/cccc1993s170

2'-Deoxyisoguanosine: Synthesis and incorporation into oligodeoxyribonucleotides

Frank Seela, Bert Gabler and Zygmunt Kazimierczuk

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  • Ding Tingting, Tang Fan, Ni Guangcheng, Liu Jiang, Zhao Hang, Chen Qianming: The development of isoguanosine: from discovery, synthesis, and modification to supramolecular structures and potential applications. RSC Adv. 2020, 10, 6223. <https://doi.org/10.1039/C9RA09427J>
  • Ingale Sachin A., Leonard Peter, Tran Quang Nhat, Seela Frank: Duplex DNA and DNA–RNA Hybrids with Parallel Strand Orientation: 2′-Deoxy-2′-fluoroisocytidine, 2′-Deoxy-2′-fluoroisoguanosine, and Canonical Nucleosides with 2′-Fluoro Substituents Cause Unexpected Changes on the Double Helix Stability. J. Org. Chem. 2015, 80, 3124. <https://doi.org/10.1021/acs.joc.5b00040>
  • Jiang Dawei, Seela Frank: Oligonucleotide Duplexes and Multistrand Assemblies with 8-Aza-2′-deoxyisoguanosine: A Fluorescent isoGd Shape Mimic Expanding the Genetic Alphabet and Forming Ionophores. J. Am. Chem. Soc. 2010, 132, 4016. <https://doi.org/10.1021/ja910020n>
  • Ramzaeva Natalya, Michalek Elisabeth, Kazimierczuk Zygmunt, Seela Frank, Rosemeyer Helmut: Hoogsteen vs. Watson–Crick Base Pairing: Incorporation of 2‐Substituted Adenine‐ and 7‐Deazaadenine 2′‐Deoxy‐β‐D‐ribonucleosides into Oligonucleotides. Chemistry & Biodiversity 2007, 4, 2725. <https://doi.org/10.1002/cbdv.200790222>
  • Li Hong, Peng Xiaohua, Leonard Peter, Seela Frank: Binding of actinomycin C1 (D) and actinomin to base-modified oligonucleotide duplexes with parallel chain orientation. Bioorganic & Medicinal Chemistry 2006, 14, 4089. <https://doi.org/10.1016/j.bmc.2006.02.002>
  • Li Hong, Peng Xiaohua, Seela Frank: Fluorescence quenching of parallel-stranded DNA bound ethidium bromide: the effect of 7-deaza-2′-deoxyisoguanosine and 7-halogenated derivatives. Bioorganic & Medicinal Chemistry Letters 2004, 14, 6031. <https://doi.org/10.1016/j.bmcl.2004.09.071>
  • Seela Frank, He Yang: 6-Aza-2‘-deoxyisocytidine:  Synthesis, Properties of Oligonucleotides, and Base-Pair Stability Adjustment of DNA with Parallel Strand Orientation. J. Org. Chem. 2003, 68, 367. <https://doi.org/10.1021/jo020507n>
  • Seela F., Kröschel R., He Y.: PARALLEL DNA CONTAINING PYRAZOLO[3,4-D]PYRIMIDINE ANALOGUES OF ISOGUANINE. Nucleosides, Nucleotides and Nucleic Acids 2001, 20, 1283. <https://doi.org/10.1081/NCN-100002537>
  • Seela Frank, Wei Changfu, Becher Georg, Zulauf Matthias, Leonard Peter: The influence of modified purine bases on the stability of parallel DNA. Bioorganic & Medicinal Chemistry Letters 2000, 10, 289. <https://doi.org/10.1016/S0960-894X(99)00679-4>
  • Seela Frank, He Yang, Wei Changfu: Parallel-stranded oligonucleotide duplexes containing 5-methylisocytosine-guanine and isoguanine-cytosine base pairs. Tetrahedron 1999, 55, 9481. <https://doi.org/10.1016/S0040-4020(99)00511-6>
  • Czochralska Barbara, Lindqvist Lars: Reaction mechanism in the photochemistry of the antileukaemic agents 2-chloro- and 2-bromo-2′-deoxyadenosine, studied by nanosecond laser flash photolysis. Journal of Photochemistry and Photobiology B: Biology 1999, 50, 28. <https://doi.org/10.1016/S1011-1344(99)00064-0>
  • Seela Frank, Wei Changfu, Melenewski Alexander, He Yang, Kröschel Rita, Feiling Elisabeth: Parallel-Stranded DNA Formed by New Base Pairs Related to the Isoguanine-Cytosine or Isocytosine-Guanine Motifs. Nucleosides and Nucleotides 1999, 18, 1543. <https://doi.org/10.1080/07328319908044781>
  • Luyten Ingrid, Herdewijn Piet: Hybridization properties of base-modified oligonucleotides within the double and triple helix motif. European Journal of Medicinal Chemistry 1998, 33, 515. <https://doi.org/10.1016/S0223-5234(98)80016-0>
  • Seela Frank., Wei Changfu., Melenewski Alexander., Feiling Elisabeth.: Parallel-Stranded Duplex DNA and Self-Assembled Quartet Structures Formed by Isoguanine and Related Bases. Nucleosides and Nucleotides 1998, 17, 2045. <https://doi.org/10.1080/07328319808004745>
  • Seela Frank, Wei Changfu: Oligonucleotides Containing Consecutive 2′‐Deoxyisoguanosine Residues: Synthesis, duplexes with parallel chain orientation, and aggregation. Helvetica Chimica Acta 1997, 80, 73. <https://doi.org/10.1002/hlca.19970800107>
  • Seela Frank, Melenewski Alexander, Wei Changfu: Parallel-stranded duplex DNA formed by a new base pair between guanine and 5-aza-7-deazaguanine. Bioorganic & Medicinal Chemistry Letters 1997, 7, 2173. <https://doi.org/10.1016/S0960-894X(97)00385-5>
  • Seela Frank, Wei Changfu, Melenewski Alexander: Oligonucleotides Containing Consecutive 2′-Deoxy-Isoguanosine Residues: Synthesis, Parallel Duplex Formation and Identification of a d(T4iG4T4) Tetraplex. Nucleosides and Nucleotides 1997, 16, 1523. <https://doi.org/10.1080/07328319708006221>
  • Seela Frank, Wei Changfu, Kazimierczuk Zygmunt: Substituent Reactivity and Tautomerism of Isoguanosine and Related Nucleosides. Helvetica Chimica Acta 1995, 78, 1843. <https://doi.org/10.1002/hlca.19950780718>
  • Seela Frank, Chen Yaoming, Bindig Uwe, Kazimierczuk Zygmunt: Synthesis of 2′‐Deoxyisoinosine and Related 2′‐Deoxyribonucleosides. Helvetica Chimica Acta 1994, 77, 194. <https://doi.org/10.1002/hlca.19940770122>
  • Seela Frank, Gabler Bert: Facile Synthesis of 2′‐Deoxyisoguanosine and Related 2′,3′‐Dideoxyribonucleosides. Helvetica Chimica Acta 1994, 77, 622. <https://doi.org/10.1002/hlca.19940770305>