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A Study of Enantioselective Reduction of para-Substituted 2-Methyl-cinnamaldehydes by Baker's Yeast

Vitomir Šunjić ; Ruđer Bošković Institute, P.O.B. 1016, HR-10001 Zagreb, Croatia
Maja Majerić ; Ruđer Bošković Institute, P.O.B. 1016, HR-10001 Zagreb, Croatia
Zdenko Hameršak ; Ruđer Bošković Institute, P.O.B. 1016, HR-10001 Zagreb, Croatia

Puni tekst: engleski, pdf (39 MB) str. 643-660 preuzimanja: 174* citiraj
APA 6th Edition
Šunjić, V., Majerić, M. i Hameršak, Z. (1996). A Study of Enantioselective Reduction of para-Substituted 2-Methyl-cinnamaldehydes by Baker's Yeast. Croatica Chemica Acta, 69 (2), 643-660. Preuzeto s https://hrcak.srce.hr/136676
MLA 8th Edition
Šunjić, Vitomir, et al. "A Study of Enantioselective Reduction of para-Substituted 2-Methyl-cinnamaldehydes by Baker's Yeast." Croatica Chemica Acta, vol. 69, br. 2, 1996, str. 643-660. https://hrcak.srce.hr/136676. Citirano 25.02.2021.
Chicago 17th Edition
Šunjić, Vitomir, Maja Majerić i Zdenko Hameršak. "A Study of Enantioselective Reduction of para-Substituted 2-Methyl-cinnamaldehydes by Baker's Yeast." Croatica Chemica Acta 69, br. 2 (1996): 643-660. https://hrcak.srce.hr/136676
Harvard
Šunjić, V., Majerić, M., i Hameršak, Z. (1996). 'A Study of Enantioselective Reduction of para-Substituted 2-Methyl-cinnamaldehydes by Baker's Yeast', Croatica Chemica Acta, 69(2), str. 643-660. Preuzeto s: https://hrcak.srce.hr/136676 (Datum pristupa: 25.02.2021.)
Vancouver
Šunjić V, Majerić M, Hameršak Z. A Study of Enantioselective Reduction of para-Substituted 2-Methyl-cinnamaldehydes by Baker's Yeast. Croatica Chemica Acta [Internet]. 1996 [pristupljeno 25.02.2021.];69(2):643-660. Dostupno na: https://hrcak.srce.hr/136676
IEEE
V. Šunjić, M. Majerić i Z. Hameršak, "A Study of Enantioselective Reduction of para-Substituted 2-Methyl-cinnamaldehydes by Baker's Yeast", Croatica Chemica Acta, vol.69, br. 2, str. 643-660, 1996. [Online]. Dostupno na: https://hrcak.srce.hr/136676. [Citirano: 25.02.2021.]

Sažetak
Reduction of a series of para-substituted 2-methyl-cinnamaldehy- des (1-7) at 20 °C and at pH = 2-3 afforded S-enantiomers of saturated alcohols 8-14 in 20-80% yield and 75 - > 99% enantiomeric excess (e.e.); at 30 °C, lower yields and e.e.s were obtained. Relative rates of the formation of allylic alcohols 15-21, catalyzed by alcohol dehydrogenase (ADH), correlate with the Hammett a+ values of para-substituents, revealing that a more efficient delocalization of the positive charge on carbonylic carbon slow down the reduction rates, whereas no correlation of the electronic properties of the substituents with the rate of C=C double bond reduction, catalyzed by enoate reductase, is observed. On reduction of 3 by dried yeast in 2H20, a,(5-carbon atoms in 10a bear 2H atoms, in accordance with the previously reported hydrogenation of selectively 2H-labeled cinnamic aldehyde and cinnamic alcohol. The accumulated data indicate that the mechanism of the enone C=C bond reduction that comprises nucleophilic attack of the hydride ion species on the (5-carbon in the first step, followed by enantioselective protonation on the a-carbon atom.

Hrčak ID: 136676

URI
https://hrcak.srce.hr/136676

Posjeta: 349 *