Oxathiaphospholane approach to the synthesis of oligodeoxyribonucleotides containing stereodefined internucleotide phosphoroselenoate function.
5'-O-DMT-deoxyribonucleoside-3'-O-(2-selena-4,4-pentamethylene-1,3,2-oxathiaphospholane) monomers, derivatives of dA, dC, dG, and T, can be resolved into pure P-diastereomers by silica gel column chromatography. They have been used for DBU-promoted, either solution- or solid-phase synthesis of P-stereodefined phosphoroselenoate analogues of oligodeoxyribonucleotides. Fast- and slow-eluting monomers are precursors of phosphoroselenoate internucleotide linkage of R(P) and S(P) absolute configuration, respectively. [reaction: see text]
Guga
Piotr
P
Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Department of Bioorganic Chemistry, Sienkiewicza 112, 90-363 Łódź, Poland.
Maciaszek
Anna
A
Stec
Wojciech J
WJ
D015394:Molecular Structure; D009711:Nucleotides / Q000737:chemistry*; D009838:Oligodeoxyribonucleotides / Q000138:chemical synthesis* / Q000737:chemistry*; D016566:Organoselenium Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D012266:Ribose / Q000031:analogs & derivatives* / Q000737:chemistry; D013237:Stereoisomerism
D009711:Nucleotides; D009838:Oligodeoxyribonucleotides; D016566:Organoselenium Compounds; C434797:oxathiaphospholane; D012266:Ribose