Enzyme-Analogue Built Polymers. XIX. Racemic Resolution on Polymers Containing Chiral Cavities

Abstract

With the aid of a chiral template molecule binding groups could be placed in a highly crosslinked polymer in s u c h a way that they are present in a chiral cavity of specific shape in a given stereochemistry. Polymers of this type possessed a high selectivity f o r racemic resolution o f the r a c e m a t e o f the template.I n the batch procedure separation factors CI a s h i g h a s 3.65 were obtained.In chromatography similar to other chromatographic racemic resolutions a s l o w m a s s transfer w a s observed. T h i s i s not due to resistance to intra-particle diffusion since similar polymers coated a s thin l a y e r s t o w i d e pore silica showed comparable behaviour.based polymers w i t h high selectivity in the batch procedure are described. Systematic investigations showed that resolutions of R, = 1 . 2 c a n be obtained. At elevated temperature the separations w e r e even better and higher retention w a s observed. T h e amount of cavities o n the surface w a s varied and a n optimum f o r chromatographic separations w a s found. New chromatographic investigations o n glycoldimethacrylate * F o r Part 1 8 , see Ref. 25) ** O n leave from Institute o f Chemical F u n d a m e n t a l s , C z e c h o s l o v a kAcademy of Sciences, 16502 P r a g u e -Suchdol (CSSR)

Chiral separation by chromatographic and electromigration techniques. A Review

“…After removing the template molecule, a chiral imprinted cavity remains, which shows high stereoselectivity to the template molecule or closely related molecules. This principle was introduced by Wulff's group [173,174]. Whereas Wulff used a covalent attachment technique based on the formation of a template-monomer complex through reversible covalent bonding, Mosbach's group [175] developed a non-covalent route making use of hydrogen bonding, electrostatic interactions, hydrophobic interactions, etc.…”

Molecularly imprinted monolithic stationary phases for liquid chromatographic separation of enantiomers and diastereomers

“…The high selectivity and low backpressure could be resolution (R ) was calculated according to the obtained using this porogenic mixture. s method proposed by Wulff et al [21]. The number of As shown in Table 2, the ratio of toluene and theoretical plates (N) was calculated by the equation dodecanol also affects the separation performance 2 N 5 16(t /w) , where w is the baseline peak width of through the change in pore structure of the mono-R eluted enantiomers.…”

Pronounced effect of temperature on racemic resolution using template‐imprinted polymeric sorbents [1]

“…Column 250X 4mm filledwith polymerE3asdescribed previously [5] was used throughout this work. The LC experiments were performed with a system consisting of syringe pump (HPP 5001, Laboratorni pristoje Praha), Model 7010 Rheodyne injector, LC column in liquid thermostatic bath, Perkin Elmer LC 85/Autocontrol spectrophotometric detector and SSI back-pressure regulator in the hydraulic line.…”