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Synthesis and Structural Study of ribo ‐Dioxaphosphorinane‐Constrained Nucleic Acid Dinucleotides ( ribo‐ α,β‐D‐CNA)
Author(s) -
Maturano Marie,
Catana DanAndrei,
Lavedan Pierre,
Tarrat Nathalie,
Saffon Nathalie,
Payrastre Corinne,
Escudier JeanMarc
Publication year - 2012
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.201101353
Subject(s) - chemistry , nucleic acid , diastereomer , stereochemistry , dimer , biochemistry , organic chemistry
With increasing interest in the control of the conformations of nucleic acids to define active riboswitch or siRNA, we present herein our efforts towards the stereocontrolled synthesis and conformational analysis of ribodinucleotides in which α and β torsional angles are constrained within a dioxaphosphorinane structure ( ribo ‐α,β‐D‐CNA). The crystal structure analysis of one α,β‐D‐CNA TU dimer demonstrates the absolute stereochemistry of the newly created asymmetric centres. NMR and CD analyses allowed complete assignment and the determination of the torsional angles in the α,β‐D‐CNA UU diastereoisomers.