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20644459550
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note
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We have defined LNA as ONs containing one or more 2′-O,4′-C-methylene bicyclic ribonucleoside LNA monomers. 2′-Amino-LNA is defined as an ON containing one or more 2′-N,4′-C-methylene bicyclic 2′-amino-LNA monomers (possibly N-derivatized, e.g., N-methylated to give 2′-methylamino-LNA).
-
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22
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0030862285
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The LNA nucleosides containing uracil and cytosine nucleobases have been synthesized independently by a linear approach: Obika, S.; Nanbu, D.; Hari, Y.; Morio, K.; In, Y.; Ishida, T.; Imanishi, T. Tetrahedron Lett. 1997, 38, 8735. Oligomers containing these pyrimidine bases have recently been reported: Obika, S.; Nanbu, D.; Hari, Y.; Andoh, J.; Morio, K.; Doi, T.; Imanishi, T. Tetrahedron Lett. 1998, 39, 5401.
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Obika, S.1
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Ishida, T.6
Imanishi, T.7
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23
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0032560835
-
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The LNA nucleosides containing uracil and cytosine nucleobases have been synthesized independently by a linear approach: Obika, S.; Nanbu, D.; Hari, Y.; Morio, K.; In, Y.; Ishida, T.; Imanishi, T. Tetrahedron Lett. 1997, 38, 8735. Oligomers containing these pyrimidine bases have recently been reported: Obika, S.; Nanbu, D.; Hari, Y.; Andoh, J.; Morio, K.; Doi, T.; Imanishi, T. Tetrahedron Lett. 1998, 39, 5401.
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24
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20644469090
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note
-
Preorganization of LNA nucleosides into a 3′-endo type conformation has been shown by X-ray crystallography (ref 5) and by NMR studies (ref 3).
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25
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The importance of hydration on duplex stability has been reported for conformationally restricted N3′-P5′-phosphoramidate DNA: Egli, M. Antisense Nucleic Acids Drug Dev. 1998, 8, 123.
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20644445253
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in press
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Preliminary thermodynamic analysis of binding between a fully modified LNA and complementary DNA has indicated a significant enthalpic advantage compared to the corresponding unmodified control: Koshkin, A. A.; Nielsen, P.; Meldgaard, M.; Rajwanshi, V. K.; Singh, S. K.; Wengel, J. J. Am. Chem. Soc., in press. A favorable entropy term has been reported for a duplex between a partly modified LNA and RNA (ref 5).
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In a communication, we have reported synthesis of the unprotected 2́-amino-LNA and 2́-thio-LNA nucleosides: Singh, S. K.; Kumar, R.; Wengel, J. J. Org. Chem. 1998, 63, 6078.
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20644471217
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note
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3, 62.9 MHz, selected signals) 172.0, 159.1, 21.7. No trace of bicyclonucleoside 3 was detected.
-
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41
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