One-pot synthesis of highly functionalized seleno amino acid derivatives.
We herein provide a new and rapid protocol to generate derivatives of seleno amino acid, including methyl selenocysteine, selenomethionine, and selenocystine. Applying the isocyanide-based multicomponent reaction Ugi-4C-5C reaction, we show that each of the commercially available seleno amino acids are good substrate for these reactions and can be used together with complementary oxocomponents and isocyanides to generate highly diverse functionalized selenium-containing compounds. These compounds might become useful tools for applications in chemical biology to elucidate the role of selenium in biochemistry.
Liu
Haixia
H
Departments of Pharmaceutical Sciences and Chemistry, University of Pittsburgh, BST3 11019, Pittsburgh, PA 1526, USA.
Dömling
Alexander
A
D003486:Cyanides / Q000737:chemistry; D017279:Selenocysteine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D012645:Selenomethionine / Q000031:analogs & derivatives* / Q000138:chemical synthesis
D003486:Cyanides; D017279:Selenocysteine; D012645:Selenomethionine