Prenyl sulfates as alkylating reagents for mercapto amino acids.
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.
Maltsev
Sergey
S
Kochetkov Laboratory of Carbohydrate Chemistry, Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russian Federation.
Sizova
Olga
O
Utkina
Natalia
N
Shibaev
Vladimir
V
Chojnacki
Tadeusz
T
Jankowski
Wieslaw
W
Swiezewska
Ewa
E
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*
D000477:Alkylating Agents; D000603:Amino Acids, Sulfur; D007202:Indicators and Reagents; D013431:Sulfates