Pyruvate decarboxylase catalysed formation of terpenoid α-hydroxy ketones

Publikation: Beitrag in FachzeitschriftArtikelForschungPeer-Review

Autoren

  • Holger Zorn
  • Martin Schüler
  • Ralf G. Berger

Organisationseinheiten

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Details

OriginalspracheEnglisch
Seiten (von - bis)341-347
Seitenumfang7
FachzeitschriftBiocatalysis and biotransformation
Jahrgang21
Ausgabenummer6
PublikationsstatusVeröffentlicht - Dez. 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.

ASJC Scopus Sachgebiete

  • Biochemie, Genetik und Molekularbiologie (insg.)
  • Biotechnologie
  • Chemische Verfahrenstechnik (insg.)
  • Katalyse
  • Biochemie, Genetik und Molekularbiologie (insg.)
  • Biochemie

Zitieren

Pyruvate decarboxylase catalysed formation of terpenoid α-hydroxy ketones. / Zorn, Holger; Schüler, Martin; Berger, Ralf G.
in: Biocatalysis and biotransformation, Jahrgang 21, Nr. 6, 12.2003, S. 341-347.

Publikation: Beitrag in FachzeitschriftArtikelForschungPeer-Review

Zorn H, Schüler M, Berger RG. Pyruvate decarboxylase catalysed formation of terpenoid α-hydroxy ketones. Biocatalysis and biotransformation. 2003 Dez;21(6):341-347. doi: 10.1080/10242420310001630173
Zorn, Holger ; Schüler, Martin ; Berger, Ralf G. / Pyruvate decarboxylase catalysed formation of terpenoid α-hydroxy ketones. in: Biocatalysis and biotransformation. 2003 ; Jahrgang 21, Nr. 6. S. 341-347.
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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

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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.

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