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S ‐Geranylated 2‐Thiouridines of Bacterial tRNAs: Chemical Synthesis and Physicochemical Properties
Author(s) -
Leszczynska Grazyna,
Sadowska Klaudia,
Bartos Paulina,
Nawrot Barbara,
Sochacka Elzbieta
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201600519
Subject(s) - chemistry , alkylation , ring (chemistry) , combinatorial chemistry , stereochemistry , organic chemistry , catalysis
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.