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Nucleic Acids Research, 1988, Vol. 16, No. 19 9165-9176
© 1988

Articles

Chemical synthesis of DNA oligomers containing cytosine arabinoside

G. Peter Beardsley*, Thomas Mikita, Melissa M. Klaus and Alexander L. Nussbaum1

Departments of Pediatrics, Medicine and Pharmacology, Yale University School of Medicine 333 Cedar Street, New Haven, CT 06510 1Department of Biological Chemistry, Harvard Medical School Boston, MA, USA

*To whom correspondence should be addressed

Received July 15, 1988. Accepted August 2, 1988.

The solid phase phospite triester synthesis of oligodeaxynucleotides containing cytosine arabinoside (araC) is described. A protected araC phosphor-amadite was prepared for the introduction of araC residues at 5' termini and internucleotide positions in DNA oligomers. These oligomers were utilized to demonstrate the formation of correct 3'–5' linkages, to test for alkaline lability at the araC site, and to study the stability of duplexes containing araC-G base pairs. For the introduction of araC residues at 3' terminal positions, a protected derivative of araC was coupled to functionalized silica. This material was used to prepare a test oligomer which was characterized enzymatically.


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