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For a general perspective on the conformational diversity produced by oligonucleotides with a six-membered sugar backbone, see
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For a general perspective on the conformational diversity produced by oligonucleotides with a six-membered sugar backbone, see: E. Lescrinier, M. Froeyen, P. Herdewijn, Nucleic Acids Res. 2003, 31, 2975-2989.
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0344326234
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The role of pyranose oligonucleotides has also been widely examined in discussions dealing with the chemical etiology of nucleic acids, see: a
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The role of pyranose oligonucleotides has also been widely examined in discussions dealing with the chemical etiology of nucleic acids, see: a) A. Eschenmoser, Science 1999, 284, 2118-2124;
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M. Froeyen, F. Morvan, J.-J. Vasseur, P. Nielsen, A. Van Aerschot, H. Rosemeyer, P. Herdewijn, Chem. Biodiversity 2007, 4, 803-817.
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14344257609
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it can be anticipated that the L-HNA system presents the proper requirements to hybridize with L-RNA with high affinity, and therefore to be conveniently used as a spiegelmer construct.
-
Given the high affinity of D-HNA for natural complements, particularly D-RNA, see refs. [6,7] and: G. Kolb, S. Reigadas, C. Boiziau, A. van Aerschot, A. Arzumanov, M. J. Gait, P. Herdewijn, J.-J. Toulmé, Biochemistry 2005, 44, 2926-2933, it can be anticipated that the L-HNA system presents the proper requirements to hybridize with L-RNA with high affinity, and therefore to be conveniently used as a spiegelmer construct.
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Kolb, G.1
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23
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65249156033
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For a review, see
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For a review, see: D. D'Alonzo, A. Guaragna, G. Palumbo, Curr. Org. Chem. 2009, 23, 71-98.
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D'Alonzo, D.1
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50549094586
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D. D'Alonzo, A. Guaragna, A. Van Aerschot, P. Herdewijn, G. Palumbo, Tetrahedron Lett. 2008, 49, 6068-6070.
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25
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33750312161
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A. Guaragna, C. Napolitano, D. D'Alonzo, S. Pedatella, G. Palumbo, Org. Lett. 2006, 8, 4863-4866.
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48249133966
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D. D'Alonzo, A. Guaragna, C. Napolitano, G. Palumbo, J. Org. Chem. 2008, 73, 5636-5639.
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28
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0033591143
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For a similar result, see
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For a similar result, see: B. Allart, R. Busson, J. Rozenski, A. Van Aerschot, P. Herdewijn, Tetrahedron 1999, 55, 6527-6546.
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0027261303
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I. Verheggen, A. Van Aerschot, S. Toppet, R. Snoeck, G. Janssen, P. Claes, J. Balzarini, E. De Clercq, P. Herdewijn, J. Med. Chem. 1993, 36, 2033-2040.
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30
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0001851070
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Preparation of 2,3-O-isopropylidene-L-glyceraldehyde, which is the starting material of the synthesis, has been reported to lead in some cases to partial racemisation, see
-
Preparation of 2,3-O-isopropylidene-L-glyceraldehyde, which is the starting material of the synthesis, has been reported to lead in some cases to partial racemisation, see: C. Hubschwerlen, J.-L. Specklin, J. Higelin, Org. Synth. 1995, 72, 1-3.
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Sabini, E.1
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70349664642
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Compounds 13 and 14 had already been evaluated as potential inhibitors of HIV (strain HIB in MT4 cells), HCMV (strain AD169 in MRC5 cells) and HSV-1 (Vero cells) infections. Unfortunately, they were inactive in these assays
-
Compounds 13 and 14 had already been evaluated as potential inhibitors of HIV (strain HIB in MT4 cells), HCMV (strain AD169 in MRC5 cells) and HSV-1 (Vero cells) infections. Unfortunately, they were inactive in these assays,
-
-
-
-
35
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70349665428
-
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In our hands, these compounds were also found inactive against parainfluenzal, reovirus-1, Sindbis and Punta Toro viruses (Vero cells), feline corona and feline herpes viruses (CRFK cells), HSV-1, HSV-2 and vaccinia virus (Hel cells), respiratory syncytial virus (HeLa cells), vesicular stomatitis virus (Hel and HeLa cells), Coxsackie B4 virus (Vero and HeLa cells), influenza A H1N1 subtype, influenza A H3N2 subtype and influenza B viruses (MDCK cells).
-
see: M. W. Andersen, S. M. Daluge, L. Kerremans, P. Herdewijn, Tetrahedron Lett. 1997, 38, 8147-8150. In our hands, these compounds were also found inactive against parainfluenzal, reovirus-1, Sindbis and Punta Toro viruses (Vero cells), feline corona and feline herpes viruses (CRFK cells), HSV-1, HSV-2 and vaccinia virus (Hel cells), respiratory syncytial virus (HeLa cells), vesicular stomatitis virus (Hel and HeLa cells), Coxsackie B4 virus (Vero and HeLa cells), influenza A H1N1 subtype, influenza A H3N2 subtype and influenza B viruses (MDCK cells).
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Andersen, M.W.1
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0001518039
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G. S. Ti, B. L. Gaffney, R. A. Jones, J. Am. Chem. Soc. 1982, 104, 1316-1319.
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84988077143
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A. Van Aerschot, T. Saison-Behmoaras, J. Rozenski, C. Hendrix, G. Schepers, G. Verhoeven, P. Herdewijn, Bull. Soc. Chim. Belges 1995, 104, 717-720.
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39
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27244432606
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Hybridisation with unnatural oligonucleotides, which has been primarily carried out for the in-depth examination of heterochiral associations, can have several applications. As mentioned before, investigations have already been carried out to study the conformational and/or chiral selection of oligonucleotides (see ref. [12]). Depending on the opportunity to have an orthogonal oligonucleotide pairing system, such as β-D-homo-DNA, useful practical applications as molecular beacons in DNA diagnostics have also been developed: C. Crey-Desbiolles, D.-R. Ahn, C.J. Leumann, Nucleic Acids Res. 2005, 33, e77.
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41
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70349671655
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10).
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10).
-
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42
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33644477832
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a) M. Egholm, O. Buchardt, P. E. Nielsen, R. H. Berg, J. Am. Chem. Soc. 1992, 114, 1895-1897;
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43
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0027364174
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b) M. Egholm, O. Buchardt, L. Christensen, C. Behrens, S. M. Freier, D. A. Driver, R. H. Berg, S. K. Kim, B. Norden, P. E. Nielsen, Nature 1993, 365, 566-568.
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Egholm, M.1
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44
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0035961034
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L. Kerremans, G. Schepers, J. Rozenski, R. Busson, A. Van Aerschot, P. Herdewijn, Org. Lett. 2001, 3, 4129-4132.
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Kerremans, L.1
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Herdewijn, P.6
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45
-
-
70349657016
-
-
This represents a further proof of the enantiomeric purity of the synthesised L-HNA.
-
This represents a further proof of the enantiomeric purity of the synthesised L-HNA.
-
-
-
-
46
-
-
70349687619
-
-
13 (Table 3).
-
13 (Table 3).
-
-
-
-
47
-
-
70349657015
-
-
13, which had very similar melting curves.
-
13, which had very similar melting curves.
-
-
-
-
48
-
-
0037065662
-
-
This result is corroborated by the X-ray analysis of ds-D-HNA, which has demonstrated that the latter forms a right-handed double helix
-
This result is corroborated by the X-ray analysis of ds-D-HNA, which has demonstrated that the latter forms a right-handed double helix: R. Declercq, A. Van Aerschot, R.J. Read, P. Herdewijn, L. Van Meervelt, J. Am. Chem. Soc. 2002, 124, 928-933.
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J. Am. Chem. Soc.
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Declercq, R.1
Van Aerschot, A.2
Read, R.J.3
Herdewijn, P.4
Van Meervelt, L.5
-
49
-
-
70349679173
-
-
The accurate amount of double strand compared to that of the single strands in each LC-MS experiment can obviously depend on how stable the complex is, and therefore this experiment should not be taken into account for a quantitative analysis.
-
The accurate amount of double strand compared to that of the single strands in each LC-MS experiment can obviously depend on how stable the complex is, and therefore this experiment should not be taken into account for a quantitative analysis.
-
-
-
|