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Nucleic Acids Research, 1992, Vol. 20, No. 13 3403-3409
© 1992

MOLECULAR BIOLOGY

Synthesis and properties of oligonucleotides containing aminodeoxythymidine units

Sergei M. Gryaznov+ and Robert L. Letsinger*

Department of Chemistry, Northwestern University Evanston, IL 60208, USA

* To whom correspondence should be addressed

Received March 20, 1992. Revised May 27, 1992. Accepted May 27, 1992.

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, TmTmTmTmTmTm-TmTmTmT(NH2) and d(TmAmTmTmCmAmGmTm-CmAmT(NH2)).

+ On leave from the M.M.Shemyakin Institute of Bioorganic Chemistry, Moscow, Russia


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