Synthesis and NMR structural analysis of 2′-OMe-uridin-3′-yl (3′,5′)-5′-O-(N-isobutyryl-2′-OMe-cytidine) methylthiophosphonates

被引:4
作者
Olejniczak, S
Potrzebowski, MJ
Wozniak, LA
机构
[1] Polish Acad Sci, Ctr Mol & Macromol Studies, Dept Bioorgan Chem, PL-90363 Lodz, Poland
[2] Polish Acad Sci, Ctr Mol & Macromol Studies, Dept Struct Studies, NMR Lab, PL-90363 Lodz, Poland
关键词
antisense agents; chirality; conformation analysis; NMR spectroscopy; oligonucleotides;
D O I
10.1002/ejoc.200300772
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Detailed analysis of the molecular structures of both the Fast-eluted and the Slow-eluted (the notation Slow and Fast corresponds to the relative mobility properties of compounds in silica gel column chromatography under normal phase conditions, see Exp. Sect. for details) diastereomers of 5'-OH-2'-OMe-uridin-3'-yl (3',5')-5'-O-(N-isobutyr-yl-2'-OMe-cytidine) methylthiophosphonate (1) was performed with the aid of H-1, C-13, 1D and 2D homo- and heteronuclear PFG (Pulse Field Gradient) NMR studies. The absolute configurations [(R-p) and (S-p)] of the diastereomers of 1 were unambiguously assigned by H-1 ROESY experiments. The pseudo-rotation parameters of the ribose ring were calculated with the aid of the PSEUDOROT program, and compared with data obtained from X-ray structure analysis. (C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004).
引用
收藏
页码:1958 / 1966
页数:9
相关论文
共 35 条