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Nucleic Acids Research, 1984, Vol. 12, No. 11 4609-4619
© 1984

CHEMISTRY

N4-Methoxydeoxycytidine triphosphate is in the imino tautomeric form and substitutes for deoxythymidine triphosphate in primed poly d[A-T] synthesis with E. coli DNA polymerase I

B. Singer1, H. Fraenkel-Conrat2, L.G. Abbott1 and S.J. Spengler2

1Laboratory of Chemical Biodynamics and Space Sciences Laboratory, University of California Berkeley, CA 94730, USA 2Department of Molecular Biology, University of California Berkeley, CA 94720, USA

Received April 11, 1984. Revised May 15, 1984. Accepted May 15, 1984.

N4-Methoxydeoxycytidine triphosphate (mo4dCTP) substitutes for dTTP in poly d[A-T] synthesis with E. coli DNA polymerase I (Pol I). In parallel experiments using as template-primer, poly d[G-C], no incorporation of [14C]mo4dC was detected. This indicates that this deoxy derivative acts as the imino tautomer, as previously found for the riboderivative. Nearest neighbor analysis of transcripts of poly d[A-T] containing mo4dC shows that the derivative substitutes for only one base. In replication, singlestranded mo4dC-containing polymers gave little misincorporation, including that of dATP which can hydrogen-bond to mo4dC in the imino form, if the methoxy group is anti to the N-3. It is therefore assumed that the methoxy group is constrained anti in a polymer such as d[A-T], but can be in thesyn form in singlestranded polymers and not recognized by DNA polymerase. mo4dC destabilizes the poly d[A-T] helix, as indicated by a lowered and less cooperative melting. Steric factors such as adjacent base displacement were invoked for similar findings with the doublestranded r(U61, mo4C39·r(A).


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