Preparation of cysteine adducts by regioselective ring-opening reactions of phenyloxirane

Heterocyclic communications

article

Alena Moulisová¹  Igor Linhart¹ 

[1] Institute of Chemical Technology, Faculty of Chemical Technology, Department of Organic Chemistry

关键词: cysteine adducts;    oxirane ring opening;    protein adducts;    styrene;    styrene oxide;   

DOI  :  10.1515/hc-2015-0042

学科分类：内科医学

来源: De Gruyter

【 摘 要 】

Regioselective ring-opening reactions of phenyloxirane by protected cysteine are described, which enable the synthesis of pure regioisomeric cysteine adducts required for bioanalytical studies on adducts of protein with styrene. The reaction catalyzed by tris(pentafluorophenyl)borane proceeds regioselectively and stereospecifically to give protected S -(2-hydroxy-1-phenylethyl)cysteine (α-adduct) with the inversion of configuration at the α-carbon. By contrast, when the same reaction is catalyzed by tetraalkylammonium fluorides, S -(2-hydroxy-2-phenylethyl)cysteine (β-adduct) is formed predominantly, and a compete racemization is observed.

【 授权许可】

CC BY|CC BY-NC-ND