Seven-Membered Ring Nucleoside Analogues: Stereoselective Synthesis and Studies on Their Conformational Properties.
The synthesis of a novel series of seven-membered ring nucleoside analogues as candidates for biological screening and gene silencing applications is described. The key step in the synthetic approach is a stereoselective synthesis of an epoxide that is used as a common synthetic intermediate to prepare functionalized oxepane nucleoside derivatives. The conformational landscape and preferred ring-puckering of selected oxepane nucleosides was also studied by NMR, X-ray crystallography, and quantum mechanical calculations.
Department of Chemistry, McGill University , 801 Sherbrooke Street West, Montreal, QC H3A 0B8, Canada.
Maryam
M
Habibian
Department of Chemistry, McGill University , 801 Sherbrooke Street West, Montreal, QC H3A 0B8, Canada.
Saúl
S
Martínez-Montero
Chemistry Department, University of Cambridge , Lensfield Road, Cambridge CB2 1EW, U.K.
Guillem
G
Portella
Department of Chemistry, McGill University , 801 Sherbrooke Street West, Montreal, QC H3A 0B8, Canada.
Zhijie
Z
Chua
Department of Chemistry, McGill University , 801 Sherbrooke Street West, Montreal, QC H3A 0B8, Canada.
D Scott
DS
Bohle
Joint BSC-CRG-IRB Programme on Computational Biology, Institute for Research in Biomedicine , Baldiri i Reixac 19, 08028 Barcelona, Spain.|Departament de Bioquímica i Biologia Molecular, Facultat de Biologia, Universitat de Barcelona , Avgda Diagonal 643, 08028 Barcelona, Spain.
Modesto
M
Orozco
Department of Chemistry, McGill University , 801 Sherbrooke Street West, Montreal, QC H3A 0B8, Canada.
Masad J
MJ
Damha
D018360:Crystallography, X-Ray; D008968:Molecular Conformation; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
D009705:Nucleosides