Study of diastereomeric thioureas formed with a new chiral derivatizing agent.
(1S,2S)-1,3-Diacetoxy-1-(4-nitrophenyl)-2-propyl isothiocyanate ((S,S)-DANI) was recently introduced as a new chiral derivatizing agent for the enantioseparation of amino compounds. In the present study, diastereomeric derivatives of racemic amino acids were formed with (S,S)-DANI. The thioureas produced were distinguished by means of infrared spectroscopy, theoretical calculations and high-performance liquid chromatography. The differences observed between the corresponding diastereomers by the independent methods are considered to prove the applicability of the new reagent in the field of enantiomer separation.
Péter
M
M
Institute of Pharmaceutical Chemistry, University of Szeged, Eötvös u. 6., 6720 Szeged, Hungary.
Perjéssy
A
A
Loos
D
D
Fülöp
F
F
D000596:Amino Acids / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid; D006860:Hydrogen Bonding; D017879:Isothiocyanates / Q000737:chemistry*; D008956:Models, Chemical; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D013055:Spectrophotometry, Infrared; D013237:Stereoisomerism; D013890:Thiourea / Q000138:chemical synthesis / Q000737:chemistry*
C408386:1,3-diacetoxy-1-(4-nitrophenyl)-2-propylisothiocyanate; D000596:Amino Acids; D017879:Isothiocyanates; D013890:Thiourea