Amino acid-based dithiazines: synthesis and photofragmentation of their benzaldehyde adducts.
Alpha-amino acids and GABA are functionalized with dithiazine rings via reaction with sodium hydrosulfide in aqueous formaldehyde. The resulting dithiazines are lithiated at -78 degrees C and reacted with benzaldehyde furnishing amino acid-based 2,5-bis-substituted dithiazines. These adducts undergo externally sensitized photofragmentation with quantum efficiency comparable to that of the parent dithiane adducts, thus offering a novel approach to amino acid-based photolabile tethers. [reaction: see text]
Kurchan
Alexei N
AN
Department of Chemistry and Biochemistry, University of Denver, Denver, CO 80208-2436, USA.
Kutateladze
Andrei G
AG