Prenyl sulfates as alkylating reagents for mercapto amino acids. | Zendy

S. D. Maltsev | Zendy; О. В. Сизова | Zendy; Natalia Utkina | Zendy; V. N. Shibaev | Zendy; Tadeusz Chojnacki | Zendy; W Jankowski | Zendy; Ewa Świeżewska | Zendy

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Prenyl sulfates as alkylating reagents for mercapto amino acids.

Author(s) -

S. D. Maltsev,

О. В. Сизова,

Natalia Utkina,

V. N. Shibaev,

Tadeusz Chojnacki,

W Jankowski,

Ewa Świeżewska

Publication year - 2008

Publication title -

acta biochimica polonica

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.452

H-Index - 78

eISSN - 1734-154X

pISSN - 0001-527X

DOI - 10.18388/abp.2008_3044

Subject(s) - prenylation , chemistry , isoprene , alkylation , reagent , organic chemistry , farnesol , stereochemistry , combinatorial chemistry , catalysis , copolymer , enzyme , polymer

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.

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