Journal
METHODS
Volume 107, Issue -, Pages 3-9Publisher
ACADEMIC PRESS INC ELSEVIER SCIENCE
DOI: 10.1016/j.ymeth.2016.02.008
Keywords
Methionine analogs; mRNA; Click chemistry; Methyltransferase; Methionine adenosyltransferase
Funding
- DFG [RE 2796/2-1]
- Fonds der Chemischen Industrie
- DFG Priority Programme [SPP1784, RE 2796/3-1]
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This paper outlines chemically and enzymatically synthesized S-adenosylmethionine (AdoMet) analogs and their use in the site-specific modification of RNA by methyltransferases, enabling the facile attachment of clickable moieties to the nucleic acid. We then focus on methodological aspects of setting up a methyltransferase-based enzymatic cascade reaction starting from methionine analogs. This strategy is applied to the one-pot modification of the mRNA cap which is subsequently derivatized in copper free and copper-catalyzed click reactions. We show that high transfer efficiencies to the cap are obtained using Se-propargyl-, hexenynyl- and azido-bearing methionine analogs. By switching to other methyltransferases our one-pot modification approach should be directly applicable to the regiospecific modification of other target molecules including nucleic acids, proteins and small molecules. (C) 2016 Elsevier Inc. All rights reserved.
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