Abstract
The enantioseparation of four phthalimide derivatives (thalidomide, pomalidomide, lenalidomide and apremilast) was investigated on five different polysaccharide-type stationary phases (Chiralpak AD, Chiralpak AS, Lux Amylose-2, Chiralcel OD and Chiralcel OJ-H) using neat methanol (MeOH), ethanol (EtOH), 1-propanol (PROP), 2-propanol (IPA) and acetonitrile (ACN) as polar organic mobile phases and also in combination. Along with the separation capacity of the applied systems, our study also focuses on the elution sequences, the effect of mobile phase mixtures and the hysteresis of retention and selectivity. Although on several cases extremely high resolutions (Rs > 10) were observed for certain compounds, among the tested conditions only Chiralcel OJ-H column with MeOH was successful for baseline-separation of all investigated drugs. Chiral selector- and mobile-phase-dependent reversals of elution order were observed. Reversal of elution order and hysteresis of retention and enantioselectivity were further investigated using different eluent mixtures on Chiralpak AD, Chiralcel OD and Lux Amylose-2 column. In an IPA/MeOH mixture, enantiomer elution-order reversal was observed depending on the eluent composition. Furthermore, in eluent mixtures, enantioselectivity depends on the direction from which the composition of the eluent is approached, regardless of the eluent pair used on amylose-based columns. Using a mixture of polar alcohols not only the selectivities but the enantiomer elution order can also be fine-tuned on Chiralpak AD column, which opens up the possibility of a new type of chiral screening strategy.
Highlights
Enantioseparations are generally more time-consuming to develop compared to achiral separations
Among the several types of chiral selectors available on the market, polysaccharide-type chiral stationary phases (CSPs) are probably the most widely applied for chiral analysis in HPLC and in supercritical fluid chromatography (SFC) [1,2,3,4,5], which makes it critical to investigate their enantiorecognition properties even further
Molecules 2022, 27, x Molecules 2022, 27, 111 these CSPs in chiral HPLC was demonstrated in normal phase [6], reversed phase [7], and in polar organic mode (PO) [8,9]
Summary
Enantioseparations are generally more time-consuming to develop compared to achiral separations. The versatile applicability of these CSPs in chiral HPLC was demonstrated in normal phase (hydrocarbon-alcohol mobile phases) [6], reversed phase (aqueous-organic mobile phases) [7], and in polar organic. Molecules 2022, 27, x Molecules 2022, 27, 111 these CSPs in chiral HPLC was demonstrated in normal phase (hydrocarbon-alcoho lofm14obile phases) [6], reversed phase (aqueous-organic mobile phases) [7], and in polar organic mode (PO) [8,9]. PPOOMM aanndd LLEENN aarree ddrruuggss ooff hhooppee iinn mmuullttiipplleemmyyeelloommaa,,wwhhilieleAAPPRRisisuuseseddfofor rththee ttrreeaattmmeenntt ooff ppssoorriiaassiiss aanndd ppssoorriiaattiicc aarrtthhrriittiiss. IInnccoonnttrraasstt tthhee iimmmmuunnoommoodduullaattoorryy ddrruuggss ((IIMMIIDDss))((TTHHAALL,,PPOOMMaannddLLEENN))aareremmarakrketeetded aepaeeonslxnsfoaprarrtnahnlaeotcdcetierioeoemtcmmdomhaaeistetrotrteraeassslssbi,ht,thiadyaldbaivuzuvioeleeeeifztbttthebooeheeteethetnehshneeueereterdfofuepaarmptsousoottregmrtirisetnnseed[rdovv2stfi5iovotvI]o.MofobIberAMIraeDamsccIsmeDeoamwmsroceirhwiozezpinachaoptthtiiitcioonoeuhtnunnenuatnod.otntfieSf.dortetnehlSvhireneeelosiversnfeaeeeeolrcvcaueaoeolvprmnmeaprpnpfepruoopcforueuarutnocnhrnhttadehdcerssehsst;tr;uehahthsderhooeiaewiewmrcsieeumepvrrvceoperuegreror,ratnr,arrtttehntdalhnyecnientecleSgyeSox-f-tehneacnhtiiora-slietpyaorfatthioenseodf TruHgAs L[2c5l]a.sAssoaf dcorungtisn[u1a2t,i2o6n–2o9f]o, uthrereacimenot fsttuhde iperserseegnatrsdtuindgyewnaans ttioosienpvaersatitgioanteotfhTeHenAaLntcioladsisscorfimdriungatsin[1g2p,2r6o–p2e9r]t,ieths eofaaimwoidf ethveaprireetsyeonftpstoulydsyacwchasartiodien-tvyepsetigCaStePsthweiethnafinvtieosdoislvcreinmtsi:naAtiCnNg ,pMroepOeHrti,eEstoOfHa,wIPidAeavnadripetryopoafnpoolly(PsaRcOchPa))riidne-PtOypme CodSeP.s wAiltohnfgivweistholvtheentsse:pAaCraNtio, nMceaOpHac,iEtytOoHf t,hIePAapapnlidedprsoypstaenmols,(PoRuOr sPt)u)diny PcoOncmenotdrea.teAsloonng wthiethetlhuetiosenpsaerqautieonncceaspiancniteyaot fstohlveeanptps laienddsiynsdteimffesr,eonutrmstiuxdtuyrecso.nHceynsttrearteessisoninthdeiffeeluretniotn speoqluyesnacccehsairnidnee-abtasseodlvceonltusmannsdwinasdaiflsfeoreexnatmminixetdu.res.
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