Degradingdehydroabietylisothiocyanate as a chiral derivatizing reagent for enantiomeric separations by capillary electrophoresis.
Abietic acid is a naturally occurring enantiomeric diterpenic acid. Its absolute optical purity and very stable stereochemistry structure makes it an excellent starting material for preparing chiral derivatizing reagents for chromatographic or electrophoretic applications. This paper describes the synthesis and evaluation of a novel chiral derivatization reagent, i.e., degradingdehydroabietylisothiocyanate (DDHAIC) derived from dehydroabietic acid. Its applicability for the enantioseparation of racemic amino acids by CE was demonstrated. DDHAIC reacted readily with amino acids at an elevated temperature (70 degrees C). The resulting derivatives were highly stable and separable by MEKC. Separation of amino acid-DDHAIC diastereomers was achieved with a running buffer consisting of 50 mM Na(2)HPO(4) (pH 9.0), 18 mM SDS, and 25% v/v ACN. Under the conditions selected, diastereomers formed from ten pairs of tested amino acid enantiomers including D/L-Asn, D/L-Met, D/L-Leu, D/L-Phe, D/L-Trp, D/L-Ser, D/L-Val, D/L-Ala, D/L-Thr, and R/S-vigabatrin were well resolved. The resolution values were in the range of 0.95-8.9.
Zhao
Shulin
S
College of Chemistry and Chemical Engineering, Guangxi Normal University, Guilin, China.
Wang
Hengshan
H
Zhang
Rongcan
R
Tang
Lidong
L
Liu
Yi-Ming
YM
D000596:Amino Acids / Q000737:chemistry / Q000302:isolation & purification*; D019075:Electrophoresis, Capillary / Q000379:methods*; D007202:Indicators and Reagents / Q000138:chemical synthesis / Q000737:chemistry*; D017879:Isothiocyanates / Q000737:chemistry*; D010616:Phenanthrenes / Q000737:chemistry*; D013237:Stereoisomerism
D000596:Amino Acids; D007202:Indicators and Reagents; D017879:Isothiocyanates; D010616:Phenanthrenes; C514702:degradingdehydroabietylisothiocyanate