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Volumn 8, Issue 8, 2007, Pages 927-932

Duplex formation of the simplified nucleic acid GNA

Author keywords

Acyclic backbone; DNA; Duplex formation; GNA; Nucleic acids; Simplified backbone

Indexed keywords

DEOXYRIBONUCLEOTIDE; DOUBLE STRANDED DNA; GLYCIDOL; GLYCOL; NUCLEIC ACID; NUCLEOTIDE; OLIGOMER; OLIGONUCLEOTIDE; PHOSPHORAMIDIC ACID DERIVATIVE; PROPYLENE; DNA; NUCLEOSIDE; ORGANOPHOSPHATE; PROPANEDIOL DERIVATIVE;

EID: 34447559698     PISSN: 14394227     EISSN: 14397633     Source Type: Journal    
DOI: 10.1002/cbic.200600435     Document Type: Article
Times cited : (72)

References (40)
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    • (S)-GNA is formally derived from the cyclic threofuranosyl nucleic acid (TNA) by removing a carbon atom and an oxygen atom from the furanose ring to render it acyclic. For the structure and function of TNA, see: K.-U. Schöning, P. Scholz, S. Guntha, X. Wu, R. Krishnamurthy, A. Eschenmoser, Science 2000, 290, 1347-1351.
    • (S)-GNA is formally derived from the cyclic threofuranosyl nucleic acid (TNA) by removing a carbon atom and an oxygen atom from the furanose ring to render it acyclic. For the structure and function of TNA, see: K.-U. Schöning, P. Scholz, S. Guntha, X. Wu, R. Krishnamurthy, A. Eschenmoser, Science 2000, 290, 1347-1351.
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    • The potential stability of duplexes consisting of an acyclic glycol backbone has been discussed before. See: H. Wippo, F. Reck, R. Kudick, M. Ramaseshan, G. Ceulemans, M. Bolli, R. Krishnamurthy, A. Eschenmoser, Bioorg. Med. Chem. 2001, 9, 2411-2428
    • The potential stability of duplexes consisting of an acyclic glycol backbone has been discussed before. See: H. Wippo, F. Reck, R. Kudick, M. Ramaseshan, G. Ceulemans, M. Bolli, R. Krishnamurthy, A. Eschenmoser, Bioorg. Med. Chem. 2001, 9, 2411-2428.
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    • See peptide nucleic acids (PNA) for a different type of acyclic oligomers that form stable duplexes: P. E. Nielsen, Acc. Chem. Res. 1999, 32, 624-630.
    • See peptide nucleic acids (PNA) for a different type of acyclic oligomers that form stable duplexes: P. E. Nielsen, Acc. Chem. Res. 1999, 32, 624-630.
  • 14
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    • For early work on the synthesis of propylene glycol nucleoside and nucleotides, see: a
    • For early work on the synthesis of propylene glycol nucleoside and nucleotides, see: a) N. Ueda, T. Kawabata, K. Takemoto, J. Heterocycl. Chem. 1971, 8, 827-829;
    • (1971) J. Heterocycl. Chem , vol.8 , pp. 827-829
    • Ueda, N.1    Kawabata, T.2    Takemoto, K.3
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    • For related glycol linkers for incorporating artificial base substitutes into DNA, see, for example: a R. Huber, N. Amann, H.-A. Wagenknecht, J. Org. Chem. 2004, 69, 744-751;
    • For related glycol linkers for incorporating artificial base substitutes into DNA, see, for example: a) R. Huber, N. Amann, H.-A. Wagenknecht, J. Org. Chem. 2004, 69, 744-751;
  • 32
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    • Similar destabilizations were observed with the related aminopropyl backbone: D. Zhou, I. M. Lagoja, J. Rozenski, R. Busson, A. Van Aerschot, P. Herdewijn, ChemBioChem 2005, 6, 2298-2304.
    • Similar destabilizations were observed with the related aminopropyl backbone: D. Zhou, I. M. Lagoja, J. Rozenski, R. Busson, A. Van Aerschot, P. Herdewijn, ChemBioChem 2005, 6, 2298-2304.
  • 33
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    • For the concept of conformational restriction of nucleosides as a measure for preorganizing oligonucleotide single strands for duplex formation, see: a M. Tarköy, C. Leumann, Angew. Chem. 1993, 105, 1516-1518;
    • For the concept of conformational restriction of nucleosides as a measure for preorganizing oligonucleotide single strands for duplex formation, see: a) M. Tarköy, C. Leumann, Angew. Chem. 1993, 105, 1516-1518;
  • 37
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    • However, Table 1 also demonstrates that it is apparently possible to fuse GNA and DNA duplexes end-to-end (see entry 6).
    • However, Table 1 also demonstrates that it is apparently possible to fuse GNA and DNA duplexes end-to-end (see entry 6).
  • 38
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    • Very similar results are obtained for the quantitative analysis of the CD signal at 270 nm as a function of the temperature. See the Supporting Information.
    • Very similar results are obtained for the quantitative analysis of the CD signal at 270 nm as a function of the temperature. See the Supporting Information.
  • 39
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    • For a comparison of the CD spectra of a DNA, RNA, and (S)-GNA duplex, see the Supporting Information.
    • For a comparison of the CD spectra of a DNA, RNA, and (S)-GNA duplex, see the Supporting Information.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.