Activation of conventional S-protecting groups of cysteine by conversion into the 3-nitro-2-pyridinesulfenyl (Npys) group

R Matsueda, S Higashida, RJ Ridge, GR Matsueda

Index: Matsueda, Rei; Higashida, Susumu; Ridge, Richard J.; Matsueda, Gary R. Chemistry Letters, 1982 , p. 921 - 924

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Citation Number: 20

Abstract

All of the conventional S-protecting groups of cysteine which were tested could be selectively converted to the 3-nitro-2-pyridinesulfenyl (Npys) group after treatment with an appropriate Npys halide. Unidirectional formation of an unsymmetrical disulfide bond is possible when Cys (Npys) is mixed with a free thiol of another Cys residue. Some of these features were exploited during the solid phase synthesis of lysine 8-vasopressin.