A new odorless procedure for the synthesis of 2'-deoxy-6-thioguanosine and its incorporation into oligodeoxynucleotides.
6-S-[2-[(2-ethylhexyl)oxycarbonyl]ethyl)}-3',5'-O-bis(tert-butyldimethylsilyl)-2'-deoxy-6-thiogua nosine (2) was synthesized in high yield from the corresponding 6-O-mesitylenesulfonyl derivative by the reaction with 2-ethylhexyl 3-mercapto-propionate. The phosphoramidite precursor derived from 2 was successfully applied to an automated DNA synthesizer to produce 2'-deoxy-6-thioguanosine containing ODN. The results showed that 2-ethylhexyl 3-mercaptopropionate is useful as an odor less reagent and also as an S-protecting group of 2'-deoxy-6-thioguanosine.
Onizuka
Kazumitsu
K
Graduate School of Pharmaceutical Sciences, Kyushu University, Fukuoka, Japan.
Taniguchi
Yosuke
Y
Sasaki
Shigeki
S
D002851:Chromatography, High Pressure Liquid; D003849:Deoxyguanosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D006151:Guanosine / Q000031:analogs & derivatives* / Q000737:chemistry; D015394:Molecular Structure; D009812:Odorants; D009838:Oligodeoxyribonucleotides / Q000138:chemical synthesis* / Q000737:chemistry; D009943:Organophosphorus Compounds / Q000737:chemistry*; D013872:Thionucleosides / Q000138:chemical synthesis* / Q000737:chemistry*
D009838:Oligodeoxyribonucleotides; D009943:Organophosphorus Compounds; D013872:Thionucleosides; C434331:phosphoramidite; D006151:Guanosine; C010438:beta-2'-deoxythioguanosine; C005783:6-thioguanosine; D003849:Deoxyguanosine