SELENOCYSTINE DERIVATIVES, ALPHA-METHYLSELENOCYSTEINE, ALPHA-METHYLSELENOCYSTEINE DERIVATIVES, AND METHODS OF MAKING AND USING SAME

摘要

Provided are selenocysteine derivatives (e.g., deuterium and tritium analogs), α-methylselenocysteine, and α-methylselenocysteine derivatives. These compounds can be incorporated in more complex chemical structures (e.g., polymers, proteins, peptides, and enzymes). Also provided are methods of making and using these compounds. The compounds can be used, for example, as drugs, chemical reagents, and redox switchable surfactants.

主权项

1. A method of making α-methylselenocysteine, a protected derivative thereof, or a derivative thereof comprising:
a) protecting the amino group, the carboxylate group, and the alcohol group of α-methylserine to form an α-methylserine having a protected amino group and protected carboxylate group; b) converting the alcohol group of the α-methylserine to a leaving group to form an α-methylserine having a protected amino group, protected carboxylate group, and leaving group; c) reacting the α-methylserine having a protected amino group, protected carboxylate group, and leaving group with a selenating reagent to form a protected α-methylselenocysteine having a protected amino group, protected carboxylate group, and a protected selenol group; and d) optionally, deprotecting the protected amino group and/or the protected carboxyl group and/or protected selenol group to form α-methylselenocysteine or a protected derivative thereof.