Introduction of 3'-terminal nucleosides having a silyl-type linker into polymer supports without base protection.
New 3'-terminal deoxyribonucleoside-loading reagents having a silyl-type linker were developed. They were effectively introduced into polymer supports under the conditions of Huisgen [3 + 2] cycloaddition without base protection. Moreover, four unmodified DNA oligomers d[TACCTAAATCCAX] (X = T, A, C, and A) and a base-labile modified DNA 12mer d[A*C*T*C*C*GT*C*T*A*C*G] 16 (A* = 6-N-acetyl-8-aza-7-deaza-2'-deoxyadenosine, C* = 4-N-acetyl-2'-deoxyctydine, T* = 2-thio-T) were successfully synthesized by cleavage of the silyl-type linker using Bu(4)NF under neutral conditions in our N-unprotected phosphoramidite method. In this paper, we also report a new reaction of chlorination of cytosine base using 1,3-dichloro-5,5-dimethylhydantoin.
Ohkubo
Akihiro
A
Department of Life Science, Tokyo Institute of Technology, Yokohama 226-8501, Japan.
Noma
Yasuhiro
Y
Aoki
Katsufumi
K
Tsunoda
Hirosuke
H
Seio
Kohji
K
Sekine
Mitsuo
M
D002384:Catalysis; D017606:Chlorine Compounds / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid; D003300:Copper / Q000737:chemistry; D004247:DNA / Q000737:chemistry; D015394:Molecular Structure; D009705:Nucleosides / Q000737:chemistry*; D011108:Polymers / Q000737:chemistry*
D017606:Chlorine Compounds; D009705:Nucleosides; D011108:Polymers; D003300:Copper; D004247:DNA