Gutenberg Open Science: Structure-function relationship of substituted bromomethylcoumarins in nucleoside specificity of RNA alkylation

Please use this identifier to cite or link to this item: http://doi.org/10.25358/openscience-7832

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DC Field	Value	Language
dc.contributor.author	Kellner, Stefanie	-
dc.contributor.author	Kollar, Laura Bettina	-
dc.contributor.author	Ochel, Antonia	-
dc.contributor.author	Ghate, Manjunath	-
dc.contributor.author	Helm, Mark	-
dc.date.accessioned	2022-10-05T08:17:50Z	-
dc.date.available	2022-10-05T08:17:50Z	-
dc.date.issued	2013	-
dc.identifier.uri	https://openscience.ub.uni-mainz.de/handle/20.500.12030/7847	-
dc.description.abstract	Selective alkylation of RNA nucleotides is an important field of RNA biochemistry, e.g. in applications of fluorescent labeling or in structural probing experiments, yet detailed structure-function studies of labeling agents are rare. Here, bromomethylcoumarins as reactive compounds for fluorescent labeling of RNA are developed as an attractive scaffold on which electronic properties can be modulated by varying the substituents. Six different 4-bromomethyl-coumarins of various substitution patterns were tested for nucleotide specificity of RNA alkylation using tRNA from Escherichia coli as substrate. Using semi-quantitative LC-MS/MS analysis, reactions at mildly acidic and slightly alkaline pH were compared. For all tested compounds, coumarin conjugates with 4-thiouridine, pseudouridine, guanosine, and uridine were identified, with the latter largely dominating. This data set shows that selectivity of ribonucleotide alkylation depends on the substitution pattern of the reactive dye, and even more strongly on the modulation of the reaction conditions. The latter should be therefore carefully optimized when striving to achieve selectivity. Interestingly, the highest selectivity for labeling of a modified nucleoside, namely of 4-thiouridine, was achieved with a compound whose selectivity was somewhat less dependent on reaction conditions than the other compounds. In summary, bromomethylcoumarin derivatives are a highly interesting class of compounds, since their selectivity for 4-thiouridine can be efficiently tuned by variation of substitution pattern and reaction conditions.	en_GB
dc.description.sponsorship	DFG, Open Access-Publizieren Universität Mainz / Universitätsmedizin	de
dc.language.iso	eng	de
dc.rights	CC BY	*
dc.rights.uri	https://creativecommons.org/licenses/by/3.0/	*
dc.subject.ddc	500 Naturwissenschaften	de_DE
dc.subject.ddc	500 Natural sciences and mathematics	en_GB
dc.title	Structure-function relationship of substituted bromomethylcoumarins in nucleoside specificity of RNA alkylation	en_GB
dc.type	Zeitschriftenaufsatz	de
dc.identifier.doi	http://doi.org/10.25358/openscience-7832	-
jgu.type.dinitype	article	en_GB
jgu.type.version	Published version	de
jgu.type.resource	Text	de
jgu.organisation.department	FB 09 Chemie, Pharmazie u. Geowissensch.	de
jgu.organisation.number	7950	-
jgu.organisation.name	Johannes Gutenberg-Universität Mainz	-
jgu.rights.accessrights	openAccess	-
jgu.journal.title	PLoS one	de
jgu.journal.volume	8	de
jgu.journal.issue	7	de
jgu.pages.alternative	e67945	de
jgu.publisher.year	2013	-
jgu.publisher.name	PLoS	de
jgu.publisher.place	Lawrence, Kan.	de
jgu.publisher.uri	http://dx.doi.org/10.1371/journal.pone.0067945	de
jgu.publisher.issn	1932-6203	de
jgu.organisation.place	Mainz	-
jgu.subject.ddccode	500	de
opus.date.modified	2018-08-14T09:22:32Z	-
opus.subject.dfgcode	06-305	-
opus.organisation.string	FB 09: Chemie, Pharmazie und Geowissenschaften: Institut für Pharmazie	de_DE
opus.identifier.opusid	23214	-
opus.institute.number	0908	-
opus.metadataonly	false	-
opus.type.contenttype	Forschungsbericht	de_DE
opus.type.contenttype	Research Report	en_EN
opus.affiliated	Helm, Mark	-
jgu.publisher.doi	10.1371/journal.pone.0067945	de
jgu.organisation.ror	https://ror.org/023b0x485	-
Appears in collections:	DFG-OA-Publizieren (2012 - 2017)

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