Synthesis of unnatural selenocystines and beta-aminodiselenides via regioselective ring-opening of sulfamidates using a sequential, one-pot, multistep strategy.

Audio, Transactions of the IRE Professio... 75(9):2910-21 (2010) PMID 20392054

A variety of N-alkyl-beta-aminodiselenides have been synthesized in high yield from sulfamidates under mild reaction conditions using potassium selenocyanate and benzyltriethylammonium tetrathiomolybdate ([BnNEt(3)](2)MoS(4)) in a sequential, one-pot, multistep reaction. The tolerance of multifarious protecting groups under the reaction conditions is discussed. The methodology was successfully extended to the synthesis of selenocystine, 3,3'-dialkylselenocystine, and 3,3'-diphenylisoselenocystine and their direct incorporation into peptides.