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Chembiochem. 2012 Oct 15;13(15):2225-33. doi: 10.1002/cbic.201200438. Epub 2012 Sep 7.

Fluorescent DNA labeling by N-mustard analogues of S-adenosyl-L-methionine.

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  • 1Department of Chemistry, Wake Forest University, 1834 Wake Forest Road, Winston-Salem, NC 27106, USA.


Azide and alkyne-functionalized N-mustard analogues of S-adenosyl-L-methionine have been synthesized and were demonstrated to undergo efficient methyltransferase-dependent DNA alkylation by M.TaqI and M.HhaI. Subsequent labeling of the DNA with a fluorophore was carried out using copper-catalyzed azide-alkyne cycloaddition chemistry and was visualized by fluorescence scanning. This work demonstrates the utility of functionalized N-mustard analogues as biochemical tools to study biological methylation and offers a facile way to site-selectively label substrates of DNA methyltransferases.

Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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