Functionalization of Cysteine Derivatives by Unsymmetrical Disulfide Bond Formation

Mateusz Szymelfejnik; Sebastian Demkowicz; Janusz Rachon; Dariusz Witt

doi:10.1055/s-2007-990853

PAPER

Functionalization of Cysteine Derivatives by Unsymmetrical Disulfide Bond Formation

Mateusz Szymelfejnik, Sebastian Demkowicz, Janusz Rachon, Dariusz Witt*
Department of Organic Chemistry, Chemical Faculty, Gdansk University of Technology, Narutowicza 11/12, 80-952 Gdansk, Poland
Fax: +48(58)3472694; e-Mail: dwitt@chem.pg.gda.pl;

Abstract

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Abstract

We have developed a convenient method for the synthesis of unsymmetrical disulfides of l-cysteine under mild conditions in good to excellent yields. The described method is based on the straightforward preparation of 5,5-dimethyl-2-thioxo-1,3,2-dioxaphosphorinane-2-sulfenyl bromide from readily available bis(5,5-dimethyl-2-thioxo-1,3,2-dioxaphosphorinan-2-yl) disulfide. The unsymmetrical disulfides can be obtained for l-cysteine derivatives and thiols bearing neutral, basic, or acidic functionalities.

Key words

unsymmetrical disulfides - l-cystine - l-cysteine - sulfenyl bromide - thiols

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