ABSTRACT
Pure 1'#,2',3',4'#,5',5''-2H6-ribonucleoside derivatives 10-14, 1'#,2',2'',3',4'#,5',5''-2H7-2'-deoxynucleoside blocks 15-18 and their natural-abundance counterparts were used to assemble partially deuterated ribonucleotide-dimers (* indicates deuteration at 1'#,2',3',4'#,5',5''(2H6)): ApU* 21, GpC* 22 and partially deuterated 2'-deoxyribonucleotide-dimers d(TpA*) 23, d(ApT*) 25, d(GpC*) 26 (* indicates deuteration at 1'#,2',2'',3',4'#,5',5''(2H7)) according to the procedure described by Földesi et al. (Tetrahedron, in press). These five partially deuterated oligonucleotides were subsequently compared with their corresponding natural-abundance counterparts by 500 MHz 1H-NMR spectroscopy to evaluate the actual NMR simplifications achieved in the non-deuterated part (1H-NMR window) as a result of specific deuterium incorporation. Detailed one-dimensional 1H-NMR (500 MHz), two-dimensional correlation spectra (DQF-COSY and TOCSY) and deuterium isotope effect on the chemical shifts of oligonucleotides have been presented.
Subject(s)
Deoxyribonucleotides/chemistry , Magnetic Resonance Spectroscopy , Protons , Ribonucleotides/chemistry , Biopolymers , Deuterium , Molecular StructureABSTRACT
Acetylquinine chemically bonded to silica was used as a chiral selector in reversed-phase chromatography for the separation of enantiomers of carboxylic acids and amino acid derivatives, e.g., 2-(4-bromophenoxy)propionic acid, warfarin and N-benzoxycarbonylphenylalanine. An organic modifier (methanol) could be used to regulate the retention without significant influence on the stereoselectivity.
