Prenyl sulfates as alkylating reagents for mercapto amino acids.

Sergey Maltsev; Olga Sizova; Natalia Utkina; Vladimir Shibaev; Tadeusz Chojnacki; Wieslaw Jankowski; Ewa Swiezewska

doi:10.18388/abp.2008_3044

Prenyl sulfates as alkylating reagents for mercapto amino acids.

Sergey Maltsev Kochetkov Laboratory of Carbohydrate Chemistry, Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russian Federation.;
Olga Sizova
Natalia Utkina
Vladimir Shibaev
Tadeusz Chojnacki
Wieslaw Jankowski
Ewa Swiezewska

DOI: https://doi.org/10.18388/abp.2008_3044

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.

Published

2008-12-16

Issue

Vol. 55 No. 4 (2008)

Section

Articles

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