PMID: 8448145Feb 9, 1993Paper

Orientation isomers of the mitomycin C interstrand cross-link in non-self-complementary DNA. Differential effect of the two isomers on restriction endonuclease cleavage at a nearby site

Biochemistry
S KumarM Tomasz

Abstract

Reductively activated mitomycin C (MC) forms DNA interstrand cross-links between two guanines at CG.CG sequences. It is predictable that such cross-links should occur in two isomeric strand orientations in duplex DNA (except when located in the center of a self-complementary duplex). This was verified by the isolation and characterization of a pair of two isomeric oligonucleotides in each case of five non-self-complementary duplexes of 8-bp length, cross-linked by MC. Isomer separation was accomplished by reverse-phase HPLC. The isomers in a pair were formed in approximately 1:1 proportion. Their structures were rigorously characterized by a two-step cross-linking procedure: first, 1''-monoalkylation of each strand, followed by conversion to a cross-linked duplex by annealing the monoalkylated strand to its complement in the presence of a reducing agent. The resulting individual authentic orientation isomers were used as standards for identification of the two isomers formed in the original (one-step) cross-linking reactions. A 16-bp duplex oligonucleotide was synthesized featuring the AluI cognate sequence, separated from a MC cross-link site by only 1 bp. Its two MC cross-linked isomers were prepared separately, and their rat...Continue Reading

References

Aug 1, 1978·Nucleic Acids Research·R A Rubin, P Modrich
Jul 28, 1992·Biochemistry·K R KumaresanA T Yeung
May 2, 1989·Biochemistry·S P TengD M Crothers
Sep 1, 1987·Proceedings of the National Academy of Sciences of the United States of America·L H HurleyC S Lee
Sep 1, 1986·Proceedings of the National Academy of Sciences of the United States of America·M TomaszG L Verdine
Sep 6, 1988·Biochemistry·T E Haran, D M Crothers
May 3, 1988·Biochemistry·A T YeungC T Chu

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Citations

Apr 5, 2002·Chembiochem : a European Journal of Chemical Biology·Albert Jeltsch
Feb 9, 2006·Chemical Reviews·David M NollPaul S Miller
Mar 1, 1996·Chemical Research in Toxicology·S M RinkM Tomasz
Feb 19, 2002·Chemical Reviews·Scott R. Rajski, Robert M. Williams

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