Laboratory of Inorganic Chemistry, Department of Chemistry and Applied Biosciences, ETH Zurich, 8093 Zürich, Switzerland.
J Org Chem. 2010 Oct 1;75(19):6696-9. doi: 10.1021/jo1011569.
Cysteamine reduces selenocystamine to form hemiselenocystamine and then cystamine. The rate constants are k(1) = 1.3 × 10(5) M(-1) s(-1); k(-1) = 2.6 × 10(7) M(-1) s(-1); k(2) = 11 M(-1) s(-1); and k(-2) = 1.4 × 10(3) M(-1) s(-1), respectively. Rate constants for reactions of cysteine/selenocystine are similar. Reaction rates of selenium as a nucleophile and as an electrophile are 2-3 and 4 orders of magnitude higher, respectively, than those of sulfur. Sulfides and selenides are comparable as leaving groups.
半胱胺将硒代半胱胺还原为胱胺。速率常数分别为 k(1) = 1.3×10(5) M(-1) s(-1); k(-1) = 2.6×10(7) M(-1) s(-1); k(2) = 11 M(-1) s(-1); k(-2) = 1.4×10(3) M(-1) s(-1)。半胱氨酸/硒代半胱氨酸的反应速率常数相似。硒作为亲核试剂和作为亲电试剂的反应速率分别比硫高 2-3 和 4 个数量级。作为离去基团,硫代和硒代的反应活性相当。