Details
| Original language | English |
|---|---|
| Pages (from-to) | 341-347 |
| Number of pages | 7 |
| Journal | Biocatalysis and biotransformation |
| Volume | 21 |
| Issue number | 6 |
| Publication status | Published - Dec 2003 |
Abstract
Enzyme extracts of the wild type yeast Zygosaccharomyces bisporus were applied for the pyruvate decarboxylase catalysed condensation of pyruvate and (R)-(+)- and (S)-(-)-perillyl aldehyde, (±)-citronellal, neral, geranial or (R)-(-)-myrtenal to form novel α-hydroxy ketones. Best yields were obtained when the transformation medium contained 25% (v/v) of the cosolvent N,N-dimethylformamide. Conversion of (R)-(+)-perillyl aldehyde to (1R)-1-hydroxy-1-[(4′R)-4′-isopropenyl-1-cyclohexen-1-yl]-2-propanon e proceeded highly stereospecifically (> 99% de), whereas the stereoselectivity was somewhat less in the transformation of (S)-(-)-perillyl aldehyde (58% de) and (R)-(-)-myrtenal (92% de). All of the new compounds imparted characteristic odour impressions as determined by means of GC-olfactometry.
Keywords
- α-Hydroxy ketones, Flavour, Terpenoid acyloins, Yeast, Zygosaccharomyces bisporus
ASJC Scopus subject areas
- Biochemistry, Genetics and Molecular Biology(all)
- Biotechnology
- Chemical Engineering(all)
- Catalysis
- Biochemistry, Genetics and Molecular Biology(all)
- Biochemistry
Cite this
- Standard
- Harvard
- Apa
- Vancouver
- BibTeX
- RIS
In: Biocatalysis and biotransformation, Vol. 21, No. 6, 12.2003, p. 341-347.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Pyruvate decarboxylase catalysed formation of terpenoid α-hydroxy ketones
AU - Zorn, Holger
AU - Schüler, Martin
AU - Berger, Ralf G.
N1 - Funding information: This work was supported by the Fonds der Che-mischen Industrie, Frankfurt. The project was part of the joint initiative project ‘‘Biologisch aktive Natur-stoffe ·/ Chemische Diversität’’ at the University of Hannover.
PY - 2003/12
Y1 - 2003/12
N2 - Enzyme extracts of the wild type yeast Zygosaccharomyces bisporus were applied for the pyruvate decarboxylase catalysed condensation of pyruvate and (R)-(+)- and (S)-(-)-perillyl aldehyde, (±)-citronellal, neral, geranial or (R)-(-)-myrtenal to form novel α-hydroxy ketones. Best yields were obtained when the transformation medium contained 25% (v/v) of the cosolvent N,N-dimethylformamide. Conversion of (R)-(+)-perillyl aldehyde to (1R)-1-hydroxy-1-[(4′R)-4′-isopropenyl-1-cyclohexen-1-yl]-2-propanon e proceeded highly stereospecifically (> 99% de), whereas the stereoselectivity was somewhat less in the transformation of (S)-(-)-perillyl aldehyde (58% de) and (R)-(-)-myrtenal (92% de). All of the new compounds imparted characteristic odour impressions as determined by means of GC-olfactometry.
AB - Enzyme extracts of the wild type yeast Zygosaccharomyces bisporus were applied for the pyruvate decarboxylase catalysed condensation of pyruvate and (R)-(+)- and (S)-(-)-perillyl aldehyde, (±)-citronellal, neral, geranial or (R)-(-)-myrtenal to form novel α-hydroxy ketones. Best yields were obtained when the transformation medium contained 25% (v/v) of the cosolvent N,N-dimethylformamide. Conversion of (R)-(+)-perillyl aldehyde to (1R)-1-hydroxy-1-[(4′R)-4′-isopropenyl-1-cyclohexen-1-yl]-2-propanon e proceeded highly stereospecifically (> 99% de), whereas the stereoselectivity was somewhat less in the transformation of (S)-(-)-perillyl aldehyde (58% de) and (R)-(-)-myrtenal (92% de). All of the new compounds imparted characteristic odour impressions as determined by means of GC-olfactometry.
KW - α-Hydroxy ketones
KW - Flavour
KW - Terpenoid acyloins
KW - Yeast
KW - Zygosaccharomyces bisporus
UR - http://www.scopus.com/inward/record.url?scp=0442310653&partnerID=8YFLogxK
U2 - 10.1080/10242420310001630173
DO - 10.1080/10242420310001630173
M3 - Article
AN - SCOPUS:0442310653
VL - 21
SP - 341
EP - 347
JO - Biocatalysis and biotransformation
JF - Biocatalysis and biotransformation
SN - 1024-2422
IS - 6
ER -