Preparation and characterization of 5-(4-hydroxy-3-nitrobenzyl)-3-phenyl-2-thiohydantoin, the phenylthiohydantoin derivative of 3-nitrotyrosine.
The phenylthiocarbamoyl derivative of 3-nitrotyrosine was synthesized according to the known Edman method and then converted to its phenylthiohydantoin derivative [5-(4-hydroxy-3-nitrobenzyl)-3-phenyl-2-thiohydantion] by incubation in 0.5M HCl for 24 h at room temperature. After drying over P2O5 the chromatographically pure substance could be obtained by double recrystallization from hot acetic acid. It could be established that a shorter incubation time leads to an incomplete conversion and higher temperatures cause polymerization of the product. The compounds could be characterized by thin-layer and high-performance liquid chromatography, melting point, elemental analysis as well as NMR- and absorption spectroscopy.
D002851:Chromatography, High Pressure Liquid; D002855:Chromatography, Thin Layer; D006827:Hydantoins / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D010669:Phenylthiohydantoin / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000302:isolation & purification; D013056:Spectrophotometry, Ultraviolet
D006827:Hydantoins; C051183:5-(4-hydroxy-3-nitrobenzyl)-3-phenyl-2-thiohydantoin; D010669:Phenylthiohydantoin