Synthesis of unnatural selenocystines and beta-aminodiselenides via regioselective ring-opening of sulfamidates using a sequential, one-pot, multistep strategy.
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.
Baig
Nasir Baig Rashid
NB
Department of Organic Chemistry, Indian Institute of Science, Bangalore-560012, Karnataka, India.
Chandrakala
R N
RN
Sai Sudhir
V
V
Chandrasekaran
Srinivasan
S
D000588:Amines / Q000138:chemical synthesis*; D003485:Cyanates / Q000737:chemistry*; D003553:Cystine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D015394:Molecular Structure; D008982:Molybdenum / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry*; D016566:Organoselenium Compounds / Q000138:chemical synthesis*; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry; D018036:Selenium Compounds / Q000737:chemistry*
C551126:3,3'-diphenylisoselenocystine; D000588:Amines; D003485:Cyanates; D009942:Organometallic Compounds; D016566:Organoselenium Compounds; D010455:Peptides; D018036:Selenium Compounds; C009226:selenocystine; D003553:Cystine; C053721:selenocyanic acid; D008982:Molybdenum