Novel route to oligo(deoxyribonucleoside phosphorothioates). Stereocontrolled synthesis of P-chiral oligo(deoxyribonucleoside phosphorothiates)

• Published in: Nucleic acids research Vol. 19; no. 21; pp. 5883 - 5888
• Main Authors: STEC, W. J, GRAJKOWSKI, A, KOZIOLKIEWICZ, M, UZNANSKI, B
• Format: Journal Article
• Language: English
• Published: Oxford Oxford University Press 11-11-1991
• Subjects: AIDS/HIV; Analytical, structural and metabolic biochemistry; Base Sequence; Biological and medical sciences; Chromatography, High Pressure Liquid; DNA, Antisense - chemical synthesis; Dna, deoxyribonucleoproteins; Electrophoresis, Polyacrylamide Gel; Fundamental and applied biological sciences. Psychology; Genes, rev - genetics; HIV - genetics; Magnetic Resonance Spectroscopy; Molecular Sequence Data; Nucleic acids; Oligodeoxyribonucleotides - chemical synthesis; Stereoisomerism; Thionucleotides - chemical synthesis; Stereoisomer; Purification; Analog; DNA; Deoxyribonucleoside; Oligodeoxyribonucleotide; Chemical synthesis
• ISSN: 0305-1048; 1362-4962
• DOI: 10.1093/nar/19.21.5883

The synthesis and separation of diastereoisomerically pure 5'-O-DMT-nucleoside 3'-O-(2-thio-1,3,2-oxathiaphospholane) allows their use as synthons in DBU-catalyzed reaction with the 5'-hydroxyl function of solid-support-bound nucleoside moiety. Since this reaction is stereospecific (greater than 99%), this novel method allows preparation of oligo(nucleoside phosphorothioates) with predetermined chirality at each P-chiral internucleotide phosphorothioate centre.