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Fluorescent DNA Labeling by N‐Mustard Analogues of S ‐Adenosyl‐ L ‐Methionine
Author(s) -
Du Yuhao,
Hendrick Charles E.,
Frye Krysta S.,
Comstock Lindsay R.
Publication year - 2012
Publication title -
chembiochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.05
H-Index - 126
eISSN - 1439-7633
pISSN - 1439-4227
DOI - 10.1002/cbic.201200438
Subject(s) - fluorophore , chemistry , dna , azide , fluorescence , alkyne , alkylation , methyltransferase , combinatorial chemistry , biochemistry , cycloaddition , click chemistry , methylation , stereochemistry , organic chemistry , catalysis , physics , quantum mechanics
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.