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Synthesis and Structure of Dinucleotides with S‐Type Sugar Puckering and Noncanonical ϵ and ζ Torsion Angle Combination (ν 2 ,ϵ,ζ‐D‐CNA)
Author(s) -
Dupouy Christelle,
Lavedan Pierre,
Escudier JeanMarc
Publication year - 2008
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.200701022
Subject(s) - chemistry , stereochemistry , diastereomer , torsion (gastropod) , hydroxymethyl , circular dichroism , nucleic acid , sugar , amino sugar , crystallography , organic chemistry , biochemistry , medicine , surgery
The synthesis of the diastereoisomers of ν 2 ,ϵ,ζ‐D‐CNA dinucleotide building units of nucleic acids and their (2′,5′)‐ν 2 ,ϵ′,ζ′‐D‐CNA analogues, in which the ϵ and ζ torsional angles are stereocontrolled by a dioxaphosphorinane ring structure (D‐CNA family) is described from a common 3‐deoxy‐3‐(hydroxymethyl)‐ D ‐allofuranose intermediate. NMR spectroscopic and circular dichroism structure analysis of ν 2 ,ϵ,ζ‐D‐CNA shows that the sugar puckering is fixed in the C‐2′‐ endo conformation and that these D‐CNA structuralelements allow stabilization of the ϵ/ζ torsion angle combinations, which are significantly different from the typical combinations observed in canonical A‐ or B‐form duplexes. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)