Journalartikel
Autorenliste: Zhang, YY; Fraatz, MA; Birk, F; Rigling, M; Hammer, A; Zorn, H
Jahr der Veröffentlichung: 2018
Seiten: 475-482
Zeitschrift: Food Chemistry
Bandnummer: 266
ISSN: 0308-8146
DOI Link: https://doi.org/10.1016/j.foodchem.2018.06.027
Verlag: Elsevier
Abstract:
Up to 35% of (R)-methyl 2-methylbutanoate (M2MB) was observed in a beverage fermented with shiitake. As M2MB naturally occurs typically in high excesses of the (S)-enantiomer, the origin of the (R)-ester was elucidated by stable isotope labeled precursor-feeding studies. (R)-2-Methylbutanoic acid was identified as the main precursor in the substrate wort. Trace amounts of (R)-M2MB were produced by transformation of unsaturated secondary metabolites (tiglic aldehyde and tiglic acid) derived from L-isoleucine. Surprisingly, shiitake esterified (R)-2-methylbutanoic acid faster to (R)-M2MB than the corresponding (S)-enantiomer. Concurrently, spontaneous non-enantioselective degradation of M2MB occurred in shiitake. This explains diverse enantiomeric ratios of M2MB and different enantiomeric ratios of 2-methylbutanoic acid and M2MB in the beverage. As the odor threshold values of (R)-and (S)-M2MB differ significantly, these findings are of high relevance for the overall flavor of the fermented beverage and elucidate the discrepancy of enantiomeric ratios of 2-alkyl-branched acids and esters reported in nature.
Zitierstile
Harvard-Zitierstil: Zhang, Y., Fraatz, M., Birk, F., Rigling, M., Hammer, A. and Zorn, H. (2018) Enantiomeric ratios of 2-methylbutanoic acid and its methyl ester: Elucidation of novel biogenetic pathways towards (R)-methyl 2-methylbutanoate in a beverage fermented with shiitake, Food Chemistry, 266, pp. 475-482. https://doi.org/10.1016/j.foodchem.2018.06.027
APA-Zitierstil: Zhang, Y., Fraatz, M., Birk, F., Rigling, M., Hammer, A., & Zorn, H. (2018). Enantiomeric ratios of 2-methylbutanoic acid and its methyl ester: Elucidation of novel biogenetic pathways towards (R)-methyl 2-methylbutanoate in a beverage fermented with shiitake. Food Chemistry. 266, 475-482. https://doi.org/10.1016/j.foodchem.2018.06.027
