Oligodeoxynucleotides containing N1-methyl-2'-deoxyadenosine and N6-methyl-2'-deoxyadenosine.
This unit describes a simple and efficient synthesis of the phosphoramidite derivative of N(1)-methyl-2'-deoxyadenosine from 2'-deoxyadenosine. The synthesis starts with the monomethoxytritylation of 2'-deoxyadenosine followed by methylation of 5'-O-protected nucleoside at N-1. Subsequent N-chloroacetylation leads to N(6)-chloroacetyl-N(1)-methyl-5'-O-(p-anisyldiphenylmethyl)-2'-deoxyadenosine, which is finally converted to its 3' phosphoramidite derivative. This phosphoramidite is used to incorporate N(1)-methyl-2'-deoxyadenosine into synthetic oligonucleotides. N-Chloroacetyl protection and controlled anhydrous deprotection conditions are used to avoid the Dimroth rearrangement.
Mikhailov
Sergey N
SN
Engelhardt Institute of Molecular Biology, Russian Academy of Sciences, Moscow, Russia.
Timofeev
Edward N
EN
Drenichev
Mikhail S
MS
Efimtseva
Ekaterina V
EV
Herdewijn
Piet
P
Roesch
Eric B
EB
Lemaitre
Marc M
MM
D002621:Chemistry / Q000379:methods*; D002851:Chromatography, High Pressure Liquid; D003839:Deoxyadenosines / Q000737:chemistry* / Q000302:isolation & purification; D009838:Oligodeoxyribonucleotides / Q000138:chemical synthesis / Q000737:chemistry* / Q000302:isolation & purification
D003839:Deoxyadenosines; D009838:Oligodeoxyribonucleotides; C058118:2'-deoxyadenosine