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1 Acta Biochimica Polonica

1 2008

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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.

tom 55

nr 4

807-813

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.