- Evaluation of the Edman degradation product of vancomycin bonded to core-shell particles as a new HPLC chiral stationary phase
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A modified macrocyclic glycopeptide-based chiral stationary phase (CSP), prepared via Edman degradation of vancomycin, was evaluated as a chiral selector for the first time. Its applicability was compared with other macrocyclic glycopeptide-based CSPs: TeicoShell and VancoShell. In addition, another modified macrocyclic glycopeptide-based CSP, NicoShell, was further examined. Initial evaluation was focused on the complementary behavior with these glycopeptides. A screening procedure was used based on previous work for the enantiomeric separation of 50 chiral compounds including amino acids, pesticides, stimulants, and a variety of pharmaceuticals. Fast and efficient chiral separations resulted by using superficially porous (core-shell) particle supports. Overall, the vancomycin Edman degradation product (EDP) resembled TeicoShell with high enantioselectivity for acidic compounds in the polar ionic mode. The simultaneous enantiomeric separation of 5 racemic profens using liquid chromatography-mass spectrometry with EDP was performed in approximately 3?minutes. Other highlights include simultaneous liquid chromatography separations of rac-amphetamine and rac-methamphetamine with VancoShell, rac-pseudoephedrine and rac-ephedrine with NicoShell, and rac-dichlorprop and rac-haloxyfop with TeicoShell.
- Hellinghausen, Garrett,Lopez, Diego A.,Lee, Jauh T.,Wang, Yadi,Weatherly, Choyce A.,Portillo, Abiud E.,Berthod, Alain,Armstrong, Daniel W.
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p. 1067 - 1078
(2018/08/01)
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- Ultrafast chiral separations for high throughput enantiopurity analysis
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Recent developments in fast chromatographic enantioseparations now make high throughput analysis of enantiopurity on the order of a few seconds achievable. Nevertheless, routine chromatographic determinations of enantiopurity to support stereochemical investigations in pharmaceutical research and development, synthetic chemistry and bioanalysis are still typically performed on the 5-20 min timescale, with many practitioners believing that sub-minute enantioseparations are not representative of the molecules encountered in day to day research. In this study we develop ultrafast chromatographic enantioseparations for a variety of pharmaceutically-related drugs and intermediates, showing that sub-minute resolutions are now possible in the vast majority of cases by both supercritical fluid chromatography (SFC) and reversed phase liquid chromatography (RP-LC). Examples are provided illustrating how such methods can be routinely developed and used for ultrafast high throughput analysis to support enantioselective synthesis investigations.
- Barhate, Chandan L.,Joyce, Leo A.,Makarov, Alexey A.,Zawatzky, Kerstin,Bernardoni, Frank,Schafer, Wes A.,Armstrong, Daniel W.,Welch, Christopher J.,Regalado, Erik L.
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supporting information
p. 509 - 512
(2017/01/13)
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- Stereoselective synthesis of (R)-(-)-mianserin
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(14bR)-2-Methyl-1,2,3,4,10,14b-hexahydrodibenzo[c,f]pyrazino[1,2-a]azepine, (R)-(-)-mianserin 1a was synthesised in several steps in good enantiomeric purity with the use of (S)-(-)-α-methylbenzylamine 5. The absolute configuration was assigned on the bas
- Pawlowska,Czarnocki,Wojtasiewicz,Maurin
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p. 3335 - 3342
(2007/10/03)
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- Synthesis and pharmacological testing of 1,2,3,4,10,14b-hexahydro-6-methoxy-2-methyldibenzo[c,f]pyrazino[1,2-a]azepin and its enantiomers in comparison with the two antidepressants mianserin and mirtazapine
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The synthesis and resolution of 1,2,3,4,10,14b-hexahydro-6-methoxy-2-methy[dibenzo[c,f]pyrazino [1,2-α]azepin (6-methoxymianserin, 6) are described. Furthermore, the in vitro and in vivo effects of 6 and its enantiomers are presented. 6 displayed high aff
- Wikstr?m, H?kan V.,Mensonides-Harsema, Marguérite M.,Cremers, Thomas I. F. H.,Moltzen, Ejner K.,Arnt, J?rn
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p. 3280 - 3285
(2007/10/03)
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- Direct gaschromatographic separation of drug racemates
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For inspection of the direct separability of synthetic drug racemates through GC/MS a uniform scheme is proposed and checked with 35 drugs and two cyclodextrin capillary columns. All investigated analytes vaporized without decomposition, 26 of them are separable in the enantiomers, among them 10 with separation to the baseline and 14 with CO-NH-structure.
- Schleuder,Duerrbeck,Jira
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p. 381 - 386
(2007/10/03)
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- 14B(R) isomers of novel tetracyclic compounds having anti-allergic and anti-asthmatic activities, and their use
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An optically active compound of formula (I): STR1 in which R3 represents groups of formula --A--COOR4, wherein A represents alkylene groups having 3 or 5 carbon atoms and R4 represents hydrogen or an alkyl group having 1 to 4 carbon atoms; or a pharmaceutically acceptable salt thereof.
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- Tetracyclic compounds having anti-allergic and anti-asthmatic activities and their use
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Compounds of formula (I): STR1 in which: Q is nitrogen or =CH--; R1 and R2 are hydrogen, alkyl, alkoxy, hydroxy, trifluoromethyl or halogen; and R3 is a substituted alkyl groups or a pharmaceutically acceptable salt thereof have valuable anti-allergic and anti-asthmatic activities. The compounds are prepared by reacting a corresponding compound where R3 is replaced by a hydrogen atom with a compound to introduce the group R3.
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