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Nucleic Acids Research 2005 33(5):1644-1652; doi:10.1093/nar/gki306
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Published online 18 March 2005

© The Author 2005. Published by Oxford University Press. All rights reserved
The online version of this article has been published under an open access model. Users are entitled to use, reproduce, disseminate, or display the open access version of this article for non-commercial purposes provided that: the original authorship is properly and fully attributed; the Journal and Oxford University Press are attributed as the original place of publication with the correct citation details given; if an article is subsequently reproduced or disseminated not in its entirety but only in part or as a derivative work this must be clearly indicated. For commercial re-use, please contact journals.permissions{at}oupjournals.org

Article

Conversion of DNA methyltransferases into azidonucleosidyl transferases via synthetic cofactors

Lindsay R. Comstock and Scott R. Rajski*

School of Pharmacy, University of Wisconsin-Madison 777 Highland Ave., Madison, WI 53705, USA

*To whom correspondence should be addressed. Tel: +608 262 7582; Fax: +608 262 5345; Email: srrajski{at}pharmacy.wisc.edu

Received January 13, 2005. Revised February 26, 2005. Accepted February 26, 2005.

Aziridine-based cofactor mimics have been synthesized and are shown to undergo methyltransferase-dependent DNA alkylation. Notably, each cofactor mimic possesses an azide functionality, to which can be attached an assortment of unnatural groups following methyltransferase-dependent DNA delivery. DNA duplexes modified with these cofactor mimics are capable of undergoing the Staudinger ligation with phosphines tethered to biological functionalities following enzymatic modification. This methodology provides a new tool by which to selectively modify DNA in a methyltransferase-dependent way. The conversion of biological methyltransferases into azidonucleosidyl transferases demonstrated here also holds tremendous promise as a means of identifying, as yet, unknown substrates of methylation.


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