title: Prenyl sulfates as alkylating reagents for mercapto amino acids.
abstract: 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 alpha-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 alpha-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.
authors.affiliation: Kochetkov Laboratory of Carbohydrate Chemistry, Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russian Federation.
authors.forename: Sergey
authors.initials: S
authors.lastname: Maltsev
authors.forename: Olga
authors.initials: O
authors.lastname: Sizova
authors.forename: Natalia
authors.initials: N
authors.lastname: Utkina
authors.forename: Vladimir
authors.initials: V
authors.lastname: Shibaev
authors.forename: Tadeusz
authors.initials: T
authors.lastname: Chojnacki
authors.forename: Wieslaw
authors.initials: W
authors.lastname: Jankowski
authors.forename: Ewa
authors.initials: E
authors.lastname: Swiezewska
mesh_terms: D000477:Alkylating Agents / Q000737:chemistry*; D000603:Amino Acids, Sulfur / Q000737:chemistry*; D007202:Indicators and Reagents / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D021241:Spectrometry, Mass, Electrospray Ionization; D013431:Sulfates / Q000737:chemistry*
chemical_list: D000477:Alkylating Agents; D000603:Amino Acids, Sulfur; D007202:Indicators and Reagents; D013431:Sulfates