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Nucleic Acids Research, 1984, Vol. 12, No. 7 3387-3404
© 1984

CHEMISTRY

Methylphosphonates as probes of protein-nucleic acid interactions

S.A. Noble*, E.F. Fisher+ and M.H. Caruthers

Department of Chemistry, University of Colorado Boulder, CO 80309, USA

Received November 28, 1983. Revised March 2, 1984. Accepted March 2, 1984.

Deoxydinucleoside methylphosphonates were prepared by chemical synthesis and were introduced stereospecifically into the .lac operator at two sites. These sites within d (ApApTpTpGpTpGpApGpCpGpGpApTpApApCpApApTpT), segment I, and d(ApApTpTpGpTpTpApTpCpCpGpCpTpCpApCpApApTpT), segment II, are indicated by p. Each segment containing a chiral methylphos phonate was annealed to the complementary unmodified segment. The interactions of these four modified lac operators with lac repressor were analyzed by the nitrocellulose filter binding assay. Introduction of either chiral phosphonate in segment II had little effect on the stability of the repressor-operator complex. When methylphosphonates were introduced into segment I, the affinity of lac repressor for the modified operators was shown to be dependent on the stereochemical configuration of the methylphosphonate.

*Present address: Department of Chemistry, Glaxo Group Research Ltd., Greenford Road, Greenford, Middlesex, UB6 0HG, UK

+present address: Fine Chemicals Division, AMGen, Inc., 1900 Oak Terrace Lane, Thousands Oaks, CA 91320, USA


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