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Prenyl sulfates as alkylating reagents for mercapto amino acids

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Maltsev S., Sizova O., Utkina N., Shibaev V., Chojnacki T., Jankowski W., Swiezewska E.
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2008
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vol. 55
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issue 4
807-813
EN
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 C10-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-SO3' 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.
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