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Consequences of P ‐Chirality in Chimeric 2′‐ O ‐Methyloligoribonucleotides with Stereoregular Methylphosphonothioate Linkages
Author(s) -
Wozniak Lucyna A.,
Janicka Magdalena,
BukowieckaMatusiak Małgorzata
Publication year - 2005
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200500395
Subject(s) - oligonucleotide , chemistry , circular dichroism , chirality (physics) , stereochemistry , dna , nuclear magnetic resonance spectroscopy , template , rna , nanotechnology , biochemistry , chiral symmetry , physics , materials science , quantum mechanics , nambu–jona lasinio model , gene , quark
Abstract Stereoregular chimeric oligonucleotides modified with diastereomerically pure methylphosphonothioate linkages interact with complementary DNA or RNA templates in a stereodependent manner. There is an unprecedented large difference in the stability of duplexes of oligonucleotides modified with alternating methylphosphonothioate linkages (Δ T m = 34 °C) that is dependent only on the stereochemistry of the methylphosphonothioate phosphorus centres. The nature of these interactions was studied by circular dichroism and NMR spectroscopy, and a thermodynamic analysis was performed. The collected data indicate that the absolute configuration at the P ‐chiral methylphosphonothioate linkages in chimeric 2′‐ O ‐methylribonucleotides could, in some cases, determine the global conformation of single–strand oligonucleotides and constrain the conformation of hybrid duplexes formed with RNA. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)