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- Title
S-Geranylated 2-Thiouridines of Bacterial tRNAs: Chemical Synthesis and Physicochemical Properties.
- Authors
Leszczynska, Grazyna; Sadowska, Klaudia; Bartos, Paulina; Nawrot, Barbara; Sochacka, Elzbieta
- Abstract
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.
- Subjects
THIOURIDINE; URIDINE; DEALKYLATION; ALKYLATION; CHEMICAL reactions; NUCLEOTIDES; NUCLEOSIDES
- Publication
European Journal of Organic Chemistry, 2016, Vol 2016, Issue 21, p3482
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201600519