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  Enhanced chemical stability of adomet analogues for improved methyltransferase-directed labeling of DNA.

Lukinavicius, G., Tomkuvienė, M., Masevičius, V., & Klimašauskas, S. (2013). Enhanced chemical stability of adomet analogues for improved methyltransferase-directed labeling of DNA. ACS Chemical Biology, 8(6), 1134-1139. doi:10.1021/cb300669x.

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Item Permalink: http://hdl.handle.net/21.11116/0000-0001-DAE4-8 Version Permalink: http://hdl.handle.net/21.11116/0000-0001-DEA6-A
Genre: Journal Article

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Lukinavicius, G.1, Author              
Tomkuvienė, M., Author
Masevičius, V., Author
Klimašauskas, S., Author
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1Laboratory of Chromatin Labeling and Imaging, Max Planck Institute for Biophysical Chemistry, Max Planck Society, ou_2616691              

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 Abstract: Methyltransferases catalyze specific transfers of methyl groups from the ubiquitous cofactor S-adenosyl-l-methionine (AdoMet) to various nucleophilic positions in biopolymers like DNA, RNA, and proteins. We had previously described synthesis and application of AdoMet analogues carrying sulfonium-bound 4-substituted but-2-ynyl side chains for transfer by methyltransferases. Although useful in certain applications, these cofactor analogues exhibited short lifetimes in physiological buffers. Examination of the reaction kinetics and products showed that their fast inactivation followed a different pathway than observed for AdoMet and rather involved a pH-dependent addition of a water molecule to the side chain. This side reaction was eradicated by synthesis of a series of cofactor analogues in which the separation between an electronegative group and the triple bond was increased from one to three carbon units. The designed hex-2-ynyl moiety-based cofactor analogues with terminal amino, azide, or alkyne groups showed a markedly improved enzymatic transalkylation activity and proved well suitable for methyltransferase-directed sequence-specific labeling of DNA in vitro and in bacterial cell lysates.

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Language(s): eng - English
 Dates: 2013
 Publication Status: Published in print
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 Rev. Method: Peer
 Identifiers: DOI: 10.1021/cb300669x
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Title: ACS Chemical Biology
Source Genre: Journal
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Pages: - Volume / Issue: 8 (6) Sequence Number: - Start / End Page: 1134 - 1139 Identifier: -