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Volumn 15, Issue 39, 2009, Pages 10121-10131

Synthesis and base pairing properties of 1′,5′-Anhydro-l- hexitol nucleic acids (L-HNA)

Author keywords

Dna analogues; Domino reactions; Hna nucleic acids; Oligonucleotides

Indexed keywords

BASE-PAIRING; CIRCULAR DICHROISM MEASUREMENTS; DOMINO REACTIONS; DUPLEX FORMATION; ENANTIOPURE; HEXITOL NUCLEIC ACIDS; HNA NUCLEIC ACIDS; L-SERIES; MODIFIED OLIGONUCLEOTIDES;

EID: 70349684629     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200901847     Document Type: Article
Times cited : (28)

References (49)
  • 3
    • 0001120760 scopus 로고    scopus 로고
    • c) E. T. Kool, Chem. Rev. 1997, 97, 1473-1488;
    • (1997) Chem. Rev. , vol.97 , pp. 1473-1488
    • Kool, E.T.1
  • 8
    • 0038239273 scopus 로고    scopus 로고
    • For a general perspective on the conformational diversity produced by oligonucleotides with a six-membered sugar backbone, see
    • 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.
    • (2003) Nucleic Acids Res. , vol.31 , pp. 2975-2989
    • Lescrinier, E.1    Froeyen, M.2    Herdewijn, P.3
  • 9
    • 0344326234 scopus 로고    scopus 로고
    • The role of pyranose oligonucleotides has also been widely examined in discussions dealing with the chemical etiology of nucleic acids, see: a
    • 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;
    • (1999) Science , vol.284 , pp. 2118-2124
    • Eschenmoser, A.1
  • 10
  • 22
    • 14344257609 scopus 로고    scopus 로고
    • 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.
    • (2005) Biochemistry , vol.44 , pp. 2926-2933
    • Kolb, G.1    Reigadas, S.2    Boiziau, C.3    Van Aerschot, A.4    Arzumanov, A.5    Gait, M.J.6    Herdewijn, P.7    Toulmé, J.-J.8
  • 30
    • 0001851070 scopus 로고
    • 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.
    • (1995) Org. Synth. , vol.72 , pp. 1-3
    • Hubschwerlen, C.1    Specklin, J.-L.2    Higelin, J.3
  • 34
    • 70349664642 scopus 로고    scopus 로고
    • 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
    • 70349665428 scopus 로고    scopus 로고
    • 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).
    • (1997) Tetrahedron Lett. , vol.38 , pp. 8147-8150
    • Andersen, M.W.1    Daluge, S.M.2    Kerremans, L.3    Herdewijn, P.4
  • 39
    • 27244432606 scopus 로고    scopus 로고
    • 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.
    • (2005) Nucleic Acids Res. , vol.33
  • 41
    • 70349671655 scopus 로고    scopus 로고
    • 10).
    • 10).
  • 45
    • 70349657016 scopus 로고    scopus 로고
    • 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 scopus 로고    scopus 로고
    • 13 (Table 3).
    • 13 (Table 3).
  • 47
    • 70349657015 scopus 로고    scopus 로고
    • 13, which had very similar melting curves.
    • 13, which had very similar melting curves.
  • 48
    • 0037065662 scopus 로고    scopus 로고
    • 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.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 928-933
    • Declercq, R.1    Van Aerschot, A.2    Read, R.J.3    Herdewijn, P.4    Van Meervelt, L.5
  • 49
    • 70349679173 scopus 로고    scopus 로고
    • 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.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.