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.
Phadnis
Prasad P
PP
Department of Inorganic and Physical Chemistry, Indian Institute of Science, Bangalore, 560 012, India.
Mugesh
G
G
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