Synthesis of L-selenodjenkolate and its degradation with methionine gamma-lyase.
A convenient method for the synthesis of a new selenium-containing amino acid, L-selenodjenkolate (3,3'-methylenediselenobis(2-aminopropionic acid)), is described. The starting material, selenocystine, was found to be prepared easily from commercially available beta-chloro-L-alanine, elemental selenium, and sodium borohydride. These synthetic procedures are useful for the preparation of the isotope-labeled compounds. The physiochemical properties of selenodjenkolate thus prepared are reported. This amino acid undergoes alpha, beta-elimination to produce pyruvate, formaldehyde, ammonia, and selenium by bacterial methionine gamma-lyase under aerobic conditions: the Vmax and Km values were determined to be 0.5 mumol/min/mg and 2.3 mM, respectively.
D000409:Alanine / Q000031:analogs & derivatives*; D000596:Amino Acids / Q000138:chemical synthesis* / Q000378:metabolism; D013437:Carbon-Sulfur Lyases / Q000378:metabolism*; D003553:Cystine / Q000031:analogs & derivatives / Q000138:chemical synthesis; D008190:Lyases / Q000378:metabolism*; D016566:Organoselenium Compounds; D012643:Selenium / Q000138:chemical synthesis* / Q000378:metabolism; D013379:Substrate Specificity
D000596:Amino Acids; D016566:Organoselenium Compounds; C009226:selenocystine; D003553:Cystine; C046966:selenodjenkolate; D008190:Lyases; D013437:Carbon-Sulfur Lyases; C021558:L-methionine gamma-lyase; D012643:Selenium; D000409:Alanine