Facile synthesis of oligonucleotide phosphoroselenoates.
Se-(2-cyanoethyl)phthalimide was synthesized from di-(2-cyanoethyl) diselenide. This reagent was found to be an efficient selenium transfer reagent in the synthesis of selenophosphates. Thus, nucleotide H-phosphonate diesters that are formed in situ through the H-phosphonate chemistry undergo quantitative reaction with Se-(2-cyanoethyl)phthalamide. The resulting Se-(2-cyanoethyl) oligonucleotide phosphoroselenoate triesters are subsequently deprotected to give oligonucleotide phosphoroselenoate diesters in excellent yields.
Tram
Kha
K
Department of Chemistry, Brock University, St. Catharines, ON, L2S 3A1, Canada.
Wang
Xiaolu
X
Yan
Hongbin
H
D002851:Chromatography, High Pressure Liquid / Q000379:methods; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D015394:Molecular Structure; D009841:Oligonucleotides / Q000138:chemical synthesis* / Q000737:chemistry; D016566:Organoselenium Compounds / Q000138:chemical synthesis* / Q000737:chemistry
D009841:Oligonucleotides; D016566:Organoselenium Compounds