Divers Stereoisomers of N-Acetylhydroxyprolinol as Sugar Substitute in Oligonucleotides |
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| Authors: | G Ceulemans A Van Aerschot P Herdewijn |
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| Institution: | Laboratorium for Medicinal Chemistry , Rega Institute for Medical research, Katholieke Universiteit Leuven , Minderbroedersstraat 10, B-3000 , Leuven , Belgium |
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| Abstract: | Abstract A detailed comparison of the hybridisation characteristics of oligonucleotides with 4-hydroxy-N-acetylprolinol or 3-hydroxy-N-acetylprolinol as sugar substitute, reveals dramatic differences. The 4-HO oligonucleotides are able to form stable complexes which are in general duplexes when natural nucleic acids are used as the complement, and the system has a strong preference for isochiral interaction. For the 3-HO oligonucleotides on the other hand complexes are generally weak, triple stranded, and often isochiral and heterochiral hybrids have a similar stability. |
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