Zdenko Hameršak

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The scope and limitation of the combined ruthenium-lipase induced dynamic kinetic resolution (DKR) through O-acetylation of racemic heteroaromatic secondary alcohols, i.e., 1-heteroaryl substituted ethanols, was investigated. After initial screening of reaction conditions, Candida antarctica lipase B (Novozyme 435, N435) together with 4-chloro-phenylacetate(More)
Ab initio calculations of the optical rotatory power of the natural cytokine modulator cytoxazone 1 and its trans-diastereomer 2, as well as the structural isomers cis-3 and trans-4 isocytoxazones, have been performed at four different wavelengths (589, 546, 435, and 405 nm) by Density Functional Theory. The calculation of ORD curves provides a reliable(More)
Amino acid sequencing and more detailed structure elucidation analysis of peptides and small proteins is a very difficult task even if state-of-the-art mass spectrometry (MS) is employed. To make this task easier, chemical derivatization methods of the N terminus with 4-sulfophenyl-isothiocyanate (SPITC) or the C terminus with(More)
Successful use of LC-NMR and LC-MS for rapid identification of an impurity in a novel antifungal drug icofungipen has been demonstrated. Complementary information obtained from the two methods made it possible to determine the structure of A1 prior to its isolation and purification. Stop-flow LC-NMR ((1)H and DQFCOSY), LC-MS and LC-MS/MS spectra have shown(More)
A series of enantiomerically pure new fragrances, derived from 2-ethylhexanol, have been prepared and their olfactory properties evaluated. The key step of the synthesis is cinchona-alkaloid-catalyzed desymmetrization of cyclic meso-anhydrides with (R)- and (S)-2-ethylhexanol and proceeded in good to excellent diastereoselectivities (92:8-98:2 dr).(More)
A range of N-protected aziridines [N-Tosyl (N-Ts), N-2-trimethylsilylethanesulfonamide (N-SES), N-tert-butoxycarbonylamido (N-Boc), and N-o-nitrobenzenesulfonamide (oNs)] were prepared in moderate to good yield and with high enantiomeric excess of both isomers starting from N-protected imines, using a sulfonium salt derived from Eliel's oxathiane. The(More)
2-Methyl-(4′-tert-butyl)cinnamaldehyde (1) was reduced by Saccharomyces cerevisiae (baker's yeast) to S-3-(4′-tert-butyl)-phenyl-2-propanol (4) in high chemical and very high optical yield (e.e. ≥99%). Chlorination of 4 to 5, and alkylation of the corresponding cyclic amines complete this short enantioselective synthesis of(More)
A series of novel pregabalin derivatives were synthesized starting from N-protected pregabalin, different amino sugars, adamantylamine, serotonin and tryptamine. New compounds were spectroscopically characterized and in vitro tested on gabapentin receptor binding assay. The serotonin-pregabalin adduct showed significant binding effect and its IC50 value was(More)
Liquid chromatography coupled with electrospray ionization mass spectrometry (ESI-MS) is routinely used in proteomics research. Mass spectrometry-based peptide analysis is performed de facto in positive-ion mode, except for the analysis of some post-translationally modified peptides (e.g., phosphorylation and glycosylation). Collected mass spectrometry data(More)
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