Ribocil
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| Names | |
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| IUPAC name
2-[1-[[2-(methylamino)pyrimidin-5-yl]methyl]piperidin-3-yl]-4-thiophen-2-yl-1''H''-pyrimidin-6-one
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| Identifiers | |
3D model (JSmol)
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CompTox Dashboard (EPA)
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| Properties | |
| C19H22N6OS | |
| Molar mass | 382.5 g/mol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
Ribocil is chemical compound which which is found to be a potent inhibitor of the FMN riboswitch, discovered by Merck & Co. through a phenotypic screen.[1] The binding mode of this small molecule to its binding site has been confirmed through the use of X-Ray crystallography.[2]
The structure of ribocil versus previously discovered binders to the FMN riboswitch makes it unique, as it is not a structural analogue to the natural ligand, flavin mononucleotide (FMN). The binding mode of this compound has some similarities with ribocil, where the same π-π sandwiching between A48 and A85 is observed, with two hydrogen bonds between the pyrimidinone carbonyl of ribocil and the A48 backbone and A99 is also conserved. Ribocil also makes two new contacts with the binding site which notably differs from FMN: a π-π stacking interaction between the aminopyrimidine of ribocil and residue G62 and an edge-face π -interaction between the thiophene moiety of ribocil A and A49.[citation needed]
References
- ↑ Howe, John A.; Wang, Hao; Fischmann, Thierry O.; Balibar, Carl J.; Xiao, Li; Galgoci, Andrew M.; Malinverni, Juliana C.; Mayhood, Todd; Villafania, Artjohn; Nahvi, Ali; Murgolo, Nicholas; Barbieri, Christopher M.; Mann, Paul A.; Carr, Donna; Xia, Ellen; Zuck, Paul; Riley, Dan; Painter, Ronald E.; Walker, Scott S.; Sherborne, Brad; de Jesus, Reynalda; Pan, Weidong; Plotkin, Michael A.; Wu, Jin; Rindgen, Diane; Cummings, John; Garlisi, Charles G.; Zhang, Rumin; Sheth, Payal R.; Gill, Charles J.; Tang, Haifeng; Roemer, Terry (2015-10-29). "Selective small-molecule inhibition of an RNA structural element". Nature. 526 (7575): 672–677. doi:10.1038/nature15542. ISSN 0028-0836. Retrieved 2017-02-02.
- ↑ Howe, John A.; Xiao, Li; Fischmann, Thierry O.; Wang, Hao; Tang, Haifeng; Villafania, Artjohn; Zhang, Rumin; Barbieri, Christopher M.; Roemer, Terry (2016-10-02). "Atomic resolution mechanistic studies of ribocil: A highly selective unnatural ligand mimic of the E. coli FMN riboswitch". RNA Biology. 13 (10): 946–954. doi:10.1080/15476286.2016.1216304. ISSN 1547-6286. PMID 27485612. Retrieved 2020-09-08.
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