Approach to the synthesis of natural and modified oligonucleotides by the phosphotriester method using o-nucleophilic intramolecular catalysis

Nucleosides, Nucleotides and Nucleic Acids

Volumn 26, Issue 8-9, 2007, Pages 1087-1093

  Efimov, Vladimir A ^a,b   Molchanova, Natalia S ^a   Chakhmakhcheva, Oksana G ^a  

^a SHEMYAKIN OVCHINNIKOV INSTITUTE OF BIOORGANIC CHEMISTRY   (Russian Federation)

^b NONE   (Russian Federation)

Author keywords

Oligoribo and deoxyribonucleotides; Phosphorothioate analogues; Stereospecific phosphotriester synthesis

Indexed keywords

OLIGODEOXYRIBONUCLEOTIDE; OLIGONUCLEOTIDE; OLIGORIBONUCLEOTIDE; PHOSPHORODITHIOIC ACID DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; SYNTHESIS;

BASE SEQUENCE; CATALYSIS; DRUG DESIGN; DRUG STABILITY; METHODS; MOLECULAR STRUCTURE; OLIGODEOXYRIBONUCLEOTIDES; OLIGONUCLEOTIDES; OLIGORIBONUCLEOTIDES;

EID: 36849045675     PISSN: 15257770     EISSN: 15322335     Source Type: Journal    
DOI: 10.1080/15257770701516268     Document Type: Article

References (5)

1. Efimov, V.; Buryakova, A.; Dubey, I.; Polushin, N.; Chakhmakhcheva, O.; Ovchinnikov, Yu. Application of new catalytic phosphate protecting groups for the highly efficient phosphotriester oligonucleotide synthesis. Nucleic Acids Res. 1986, 14, 6526-6540.
2. Polushin, N.; Smirnov, I.; Verentchikov, A.; Coull, J. Synthesis of oligonucleotides containing 2′-azido- and 2′-amino-2′- deoxyuridine using phosphotriester chemistry. Tetrahedrom Lett. 1996, 3227-3230.
3. Almer, H.; Szabo, T.; Stawinski, J. A new approach to stereospecific synthesis of P-chiral phosphorothioates. Preparation of diastereomeric dithymidyl-(3′-5′) phosphorothioates. Chem. Commun. 2004, 290-291.
4. Reese, C.; Yan, H. Solution phase synthesis of ISIS 2922 (Vitravene) by the modified H-phosphonate approach. J. Chem. Soc. Perkin Trans. 2002, 1, 2619-2633.
5. Efimov, V.; Kalinkina, A.; Chakhmakhcheva, O.; Schmaltz Hill, T.; Jayaraman, K. New efficient sulfurizing reagents for the preparation of oligodeoxyribonucleotide phosphorothioate analogues. Nucleic Acids Res. 1995, 23, 4029-4033.