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Regular paper on-line at: Prenyl sulfates as alkylating reagents for mercapto amino acids

By Sergey Maltsev, Olga Sizova, Natalia Utkina, Vladimir Shibaev, Tadeusz Chojnacki, Wieslaw Jankowski and Ewa Swiezewska


A new methodology for prenylation of thiol compounds has been developed. The approach is based on the use of prenyl sulfates as new reagents for S-prenylation of benzenethiol and cysteamine in aqueous systems. The C 10-prenols geraniol and nerol that differ in the configuration (E or Z, correspondingly) of the α-isoprene unit were efficiently O-sulfated in the presence of a pyridine-SO 3, complex. The obtained geranyl and neryl sulfates were tested as alkylating agents. These compounds were chosen to reveal the influence of the α-isoprene unit configuration on their alkylation (prenylation) ability. S-Geranyl cysteine was prepared to demonstrate the applicability of this method for prenylation of peptides containing mercapto amino acids

Topics: S-prenylation, lipidated amino acids, geraniol, nerol, cysteamine, cysteine
Year: 2008
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