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Nucleic Acids Research, 1990, Vol. 18, No. 15 4355-4360
© 1990

CHEMISTRY

A protected biotin containing deoxycytidine building block for solid phase synthesis of biotinylated oligonucleotides

Uwe Pieles, Brian S. Sproat* and Gabor M. Lamm

European Molecular Biology Laboratory Meyerhofstraße 1, D-6900 Heidelberg, FRG

*To whom correspondence should be addressed

Received June 1, 1990. Revised July 11, 1990. Accepted July 11, 1990.

The synthesis of a modified 2'-deoxycytidine-3'-Ophosphoramidite carrying an N-t-butylbenzoyl protected biotin on a long polar spacer arm attached to the 4-N position is described. The presence of the bulky lipophilic t-butylbenzoyl protecting group enables the direct solid phase synthesis of biotinylated oligoribonucleotides and a variety of analogues in high yield without modification of the biotin moiety. Biotinylated antisense oligonucleotides incorporating this new derivative allow convenient isolation and purification of ribonucleic acid-protein complexes. The kinetics of biotin binding to streptavidin agarose is facilitated by the long polar spacer arm.


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