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7
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0042267246
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Angew. Chem. Int. Ed. 2003, 42, 3204-3206.
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(2003)
Chem. Int. Ed
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Angew1
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9
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16244417170
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L. Zhang, A. E. Peritz, E. Meggers, J. Am. Chem. Soc. 2005, 127, 4174-4175.
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J. Am. Chem. Soc
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Zhang, L.1
Peritz, A.E.2
Meggers, E.3
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11
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0034680801
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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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-
-
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12
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0034835910
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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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-
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13
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0032766821
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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.
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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.
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-
-
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14
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84980314040
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For early work on the synthesis of propylene glycol nucleoside and nucleotides, see: a
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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;
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J. Heterocycl. Chem
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Ueda, N.1
Kawabata, T.2
Takemoto, K.3
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15
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2742542700
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b) T. Seita, K. Yamauchi, M. Kinoshita, M. Imoto, Bull. Chem. Soc. Jpn. 1972, 45, 926-928;
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Bull. Chem. Soc. Jpn
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Seita, T.1
Yamauchi, K.2
Kinoshita, M.3
Imoto, M.4
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16
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0342417260
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c) T. Seita, M. Kinoshita, M. Imoto, Bull. Chem. Soc. Jpn. 1973, 46, 1572-1573;
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Bull. Chem. Soc. Jpn
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Seita, T.1
Kinoshita, M.2
Imoto, M.3
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20
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0010472244
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g) A. Holý, I. Rosenberg, H. Dvořáková, Collect. Czech. Chem. Commun. 1989, 54, 2470-2501.
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Collect. Czech. Chem. Commun
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Holý, A.1
Rosenberg, I.2
Dvořáková, H.3
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21
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0028962640
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P. Nielsen, L. H. Dreiøe, J. Wengel, Bioorg. Med. Chem. 1995, 3, 19-28.
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(1995)
Bioorg. Med. Chem
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Nielsen, P.1
Dreiøe, L.H.2
Wengel, J.3
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23
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0028784356
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P. W. Davis, T. A. Vickers, L. Wilson-Lingardo, J. R. Wyatt, C. J. Guinosso, Y. S. Sanghvi, E. A. DeBaets, O. L. Acevedo, P. D. Cook, D. J. Ecker, J. Med. Chem. 1995, 38, 4363-4366.
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J. Med. Chem
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Davis, P.W.1
Vickers, T.A.2
Wilson-Lingardo, L.3
Wyatt, J.R.4
Guinosso, C.J.5
Sanghvi, Y.S.6
DeBaets, E.A.7
Acevedo, O.L.8
Cook, P.D.9
Ecker, D.J.10
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24
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0842285790
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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;
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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;
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-
-
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28
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0026656802
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b) M. Azymah, C. Chavis, M. Lucas, F. Morvan, J.-L. Imbach, Nucleosides Nucleotides 1992, 11, 1241-1255;
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Nucleosides Nucleotides
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Azymah, M.1
Chavis, C.2
Lucas, M.3
Morvan, F.4
Imbach, J.-L.5
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29
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0027254689
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c) F. Vandendriessche, K. Augustyns, A. Van Aerschot, R. Busson, J. Hoogmartens, P. Herdewijn, Tetrahedron 1993, 49, 7223-7238;
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Tetrahedron
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Vandendriessche, F.1
Augustyns, K.2
Van Aerschot, A.3
Busson, R.4
Hoogmartens, J.5
Herdewijn, P.6
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30
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0028352074
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d) P. Nielsen, F. Kirpekar, J. Wengel, Nucleic Acids Res. 1994, 22, 703-710;
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Nucleic Acids Res
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Nielsen, P.1
Kirpekar, F.2
Wengel, J.3
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32
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33645131181
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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.
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33
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34547584443
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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;
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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;
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-
-
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37
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34547577120
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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).
-
-
-
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38
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34547606160
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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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34547601400
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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.
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40
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0033565267
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S. Nakano, M. Fujimoto, H. Hara, N. Sugimoto, Nucleic Acids Res. 1999, 27, 2957-2965.
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Nucleic Acids Res
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Nakano, S.1
Fujimoto, M.2
Hara, H.3
Sugimoto, N.4
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