Synthesis and properties of oligonucleotides containing aminodeoxythymidine units.
Procedures are described for synthesis via solid support methodology of oligonucleotide analogues derived in part from 3'-amino-3'-deoxythymidine or 5'-amino-5'-deoxythymidine. Oligothymidylate decamers terminated with a 3'-amino group or containing a 3'-NHP(O)(O-)O-5' internucleoside link are found to form unusually stable complexes with poly(dA), poly(A), and oligo(dA). For related derivatives of 5'-amino-5'-deoxythymidine enhancement is less or absent, and in the case of multiple substitution destabilization of the heteroduplex may be observed. That the effect of the 3'-amino group is general for oligonucleotide derivatives is indicated by enhanced Tm values for heteroduplex complexes of the mixed-base oligomer, d(TATTCAGTCAT(NH2)), and the methyl phosphonate derivatives, TmTmTmTmTmTmTmTmTmT(NH2) and d(TmAmTmTmCmAmGmTmCmAmT(NH2)).
Gryaznov
S M
SM
Department of Chemistry, Northwestern University, Evanston, IL 60208.
Letsinger
R L
RL
D001483:Base Sequence; D002851:Chromatography, High Pressure Liquid; D015224:Dideoxynucleosides / Q000138:chemical synthesis*; D008969:Molecular Sequence Data; D009838:Oligodeoxyribonucleotides / Q000138:chemical synthesis*; D013696:Temperature
D015224:Dideoxynucleosides; D009838:Oligodeoxyribonucleotides; C024082:5'-amino-5'-deoxythymidine