Enantioselective drug monitoring of (R)- and (S)-propranolol in human plasma via derivatization with optically active (R,R)-O,O-diacetyl tartaric acid anhydride

Reversed‐phase high‐performance liquid chromatographic enantioresolution of six β‐blockers using dinitrophenyl‐l‐Pro‐N‐hydroxysuccinimide ester, N‐succinimidyl‐(S)‐2‐(6‐methoxynaphth‐2‐yl) propionate and twelve variants of Sanger's reagent as chiral derivatizing reagents

“…Several chiral derivatizing reagents (CDR) have been used for indirect HPLC separation of enantiomers of β-blockers, e.g. (S)-(−)-or (R)-(+)-1-phenylethylisocyanate (Thompson et al, 1982), 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl isothiocyanate (Eisenberg et al, 1989, N-trifluoroacetyl-l-prolyl chloride (Hermansson and Von Bahr, 1980), (R)-(−)-1-(1-naphthyl)ethyl isocyanate (Darmon and Thenot, 1986), tert-butoxycarbonyl-L-leucine anhydride (Guttendorf et al, 1989), (R,R)-O,O′-diacetyltartaric acid anhydride (Lindner et al, 1989), 2,3,4-tri-O-acetyl-α-D-arabinopyranosyl isothiocyanate (Sedman and Gal, 1983) and different chloroformates (Schitthenner et al, 1989;Mehvar, 1989).…”

Measurement of Urinary d- and l-2-Hydroxyglutarate Enantiomers by Stable-Isotope-Dilution Liquid Chromatography–Tandem Mass Spectrometry after Derivatization with Diacetyl-l-Tartaric Anhydride

“…The derivatization reagent DATAN is not expensive, has great separation potential, and is a good leaving group in the collision cell, allowing the use of low collision energy and thereby increasing the selectivity of the measurement. In spite of these unique characteristics, the reagent has rarely been mentioned in the literature (12)(13)(14)(15). Other biochemically important hydroxyacids, i.e., d/l-lactate, d/l-glycerate, and d/l-3hydroxybutyrate, can also be separated enantiomerically by use of DATAN as the derivatizing reagent, without the need to change chromatographic conditions (data not shown).…”

Chiral derivatization reagents for drug enantioseparation by high‐performance liquid chromatography based upon pre‐column derivatization and formation of diastereomers: enantioselectivity and related structure

“…With tartaric acid anhydrides as CDRs the derivatization reactions of b-blockers are carried out in aprotic media after the amine functions are protected by ion pair formation with trifluoro acetic acid. The diastereomeric monoesters are easily separable by reversed phase liquid chromatography, due to the formation of intramolecular hydrogen bonds and the resulting intramolecular zwitterionic ring (Lindner et al, 1989). Using DBTAAN (40) as a CDR, separation of 15 different b-blockers was achieved.…”

“…When the amine function in a parent (R,S)-alkanolamine molecule is substituted by either an isopropyl or a tert-butyl group, the structural dependency of the chromatographic stereoselectivity of diasteromers can also be investigated by varying the chain length of the methylene space groups between the alcohol and the amine function. The result showed that the a-values of such derivatives drop quite significantly with increase of chain length of the methylene space groups, probably resulting from the change of the intramolecular ring size (Lindner et al, 1989). Hermansson and Bahr (1982) synthesized the symmetrical anhydrides of tert-butoxycarbonyl-L-leucine (Boc-L-Leu) and its alanine analog, tert-butoxycarbonyl-Lalanine (Boc-L-Ala), and applied then to quantitate alprenolol and matoprolol in plasma.…”