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Nucleic Acids Research, 1989, Vol. 17, No. 18 7179-7186
© 1989

CHEMISTRY

A new and versatile reagent for incorporating multiple primary aliphatic amines into synthetic oligonucleotides

Paul S. Nelson, Rivka Sherman-Gold1 and Roy Leon

Organic Chemistry Division, Clontech Laboratories Inc., 3040 Fabian Way, Palo Alto, CA 94303 1Biogrowth Inc. 3065 Atlas Road, Richmond, CA 94806, USA

Received August 1, 1989. Accepted August 11, 1989.

A novel and versatile phosphorarnidite, N-Fmoc-O1-DMT-O2-cyanoethoxydiiopropylamino-phosphinyl-3-amino-1,2-propanediol (1, Fig. 1), has been synthesized and used to incorporate primary aliphatic amines into synthetic oligonucleotides. Its convenient preparation and use in solid phase oligonucleotide synthesis is described. Using phosphoramidite 1, an amino-modified oligonucleotide probe complementary to M13mp18 DNA was constructed with five primary amines attached to the 5'-terminus. The amino-modified oligonucleotide was subsequently labeled with biotin and employed in a dot-blot hybridization assay. As little as 0.5 ng of M13mp18 target DNA was colorimetrically detected


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