jo048136t_si_001.cif (50.17 kB)
Constrained Nucleic Acids (CNA). Part 2. Synthesis of Conformationally Restricted Dinucleotide Units Featuring Noncanonical α/β/γ or δ/ε/ζ Torsion Angle Combinations
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posted on 2005-03-04, 00:00 authored by Ingrid Le Clézio, Heinz Gornitzka, Jean-Marc Escudier, Alain VigrouxFour dinucleotide building units of nucleic acids in which three out of six backbone torsion angles
are included in a dioxaphosphorinane ring structure (D-CNA family) have been synthesized: two
diastereoisomeric α,β,γ-D-CNA {cis and trans} and two diastereoisomeric δ,ε,ζ-D-CNA {(SC4‘,RP)
and (SC4‘,SP)}. The structural analysis of these conformationally restricted dinucleotides, using NMR
spectroscopy and X-ray crystallography, shows that these D-CNA structural elements allow the
stabilization of torsion angle combinations, α/β/γ and δ/ε/ζ, that are significantly different from
those typically observed in canonical A- or B-form duplexes.
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RestrictedPart 2. Synthesisdinucleotide building unitsUnitsFeaturingacidCombinationConstrained Nucleic Acidsbackbone torsion anglesdiastereoisomericcrystallographydioxaphosphorinane ring structurecanonicalstabilizationNoncanonicalCNANMR spectroscopyConformationallyconformationallyR Pduplexetorsion angle combinationstrananalysisDinucleotideTorsion
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