Internally stabilized selenocysteine derivatives: syntheses, 77Se NMR and biomimetic studies.
Selenocystine ([Sec]2) and aryl-substituted selenocysteine (Sec) derivatives are synthesized, starting from commercially available amino acid l-serine. These compounds are characterized by a number of analytical techniques such as NMR (1H, 13C and 77Se) and TOF mass spectroscopy. This study reveals that the introduction of amino/imino substituents capable of interacting with selenium may stabilize the Sec derivatives. This study further suggests that the oxidation-elimination reactions in Sec derivatives could be used for the generation of biologically active selenols having internally stabilizing substituents.
Department of Inorganic and Physical Chemistry, Indian Institute of Science, Bangalore, 560 012, India.
Prasad P
PP
Phadnis
G
G
Mugesh
D032701:Biomimetics; D007097:Imines / Q000737:chemistry; D007554:Isotopes; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D010084:Oxidation-Reduction; D012643:Selenium / Q000737:chemistry*; D017279:Selenocysteine / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000494:pharmacology; D012694:Serine / Q000737:chemistry
D007097:Imines; D007554:Isotopes; D017279:Selenocysteine; D012694:Serine; D012643:Selenium