期刊
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
卷 2016, 期 21, 页码 3482-3485出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201600519
关键词
Conformation analysis; Geranylation; Lipophilicity; Nucleosides; Sulfur
资金
- National Science Centre in Poland [UMO-2014/13/B/ST5/03979]
- Lodz University of Technology
- Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences
Herein, we report the first synthesis of two recently discovered, prenylated 2-thiouridine derivatives, 5-methylaminomethyl-S-geranyl-2-thiouridine (mnm5geS2U) and 5-carboxymethylaminomethyl-S-geranyl-2-thiouridine (cmnm5geS2U). S-Geranylated 2-thiouridines were obtained by S-alkylation of the parent (c)mnm5S2U nucleosides suitably protected at their C5-alkylamino function. Comparative physicochemical studies of S2U, mnm5S2U, and cmnm5S2U and their S-geranylated derivatives revealed unique highly hydrophobic properties of the geranylated species and their increased C2-endo sugar ring puckering in comparison to their parent 2-thiouridines.
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