Biotransformation of γ-terpinene using Stemphylium botryosum (Wallroth) yields p-mentha-1,4-dien-9-ol, a novel odorous monoterpenol

Publikation: Beitrag in FachzeitschriftArtikelForschungPeer-Review

Autoren

  • Ulrich Krings
  • Bianca Brauer
  • Rüdiger Kaspera
  • Ralf Berger

Organisationseinheiten

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Details

OriginalspracheEnglisch
Seiten (von - bis)457-463
Seitenumfang7
FachzeitschriftBiocatalysis and biotransformation
Jahrgang23
Ausgabenummer6
PublikationsstatusVeröffentlicht - Nov. 2005

Abstract

A wild strain of Stemphylium botryosum, when grown submerged in the presence of γ-terpinene (1), yielded the novel highly odour active terpene alcohol (2), whose structure was established by spectroscopic means as p-mentha-1,4-dien-9-ol. During cultivation (2) was further oxidized, predominantly to the corresponding aromatic alcohol p-cymene-9-ol (5). The enantioselective enzymatic introduction of the hydroxyl group at the non-activated C9 of (1) resulted in an enantiomeric excess (ee) of 74% for (2) and 70% for (5), respectively.

ASJC Scopus Sachgebiete

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

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Biotransformation of γ-terpinene using Stemphylium botryosum (Wallroth) yields p-mentha-1,4-dien-9-ol, a novel odorous monoterpenol. / Krings, Ulrich; Brauer, Bianca; Kaspera, Rüdiger et al.
in: Biocatalysis and biotransformation, Jahrgang 23, Nr. 6, 11.2005, S. 457-463.

Publikation: Beitrag in FachzeitschriftArtikelForschungPeer-Review

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title = "Biotransformation of γ-terpinene using Stemphylium botryosum (Wallroth) yields p-mentha-1,4-dien-9-ol, a novel odorous monoterpenol",
abstract = "A wild strain of Stemphylium botryosum, when grown submerged in the presence of γ-terpinene (1), yielded the novel highly odour active terpene alcohol (2), whose structure was established by spectroscopic means as p-mentha-1,4-dien-9-ol. During cultivation (2) was further oxidized, predominantly to the corresponding aromatic alcohol p-cymene-9-ol (5). The enantioselective enzymatic introduction of the hydroxyl group at the non-activated C9 of (1) resulted in an enantiomeric excess (ee) of 74% for (2) and 70% for (5), respectively.",
keywords = "γ-terpinene, Biotransformation, p-cymene-9-ol, p-mentha-1,4-dien-9-ol, Stemphylium botryosum",
author = "Ulrich Krings and Bianca Brauer and R{\"u}diger Kaspera and Ralf Berger",
note = "Funding information: This project was supported by Deutsche Bundesstif-tung Umwelt, DBU, as part of the joint initiative project {\textquoteleft}Biotechnologie in der Lebensmittelindustrie zum produktionsintegrierten Umweltschutz (BIOL){\textquoteright}. We thank E. Hofer of the Centre of Organic Chemistry of the University of Hannover for his help in NMR analyses.",
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journal = "Biocatalysis and biotransformation",
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Download

TY - JOUR

T1 - Biotransformation of γ-terpinene using Stemphylium botryosum (Wallroth) yields p-mentha-1,4-dien-9-ol, a novel odorous monoterpenol

AU - Krings, Ulrich

AU - Brauer, Bianca

AU - Kaspera, Rüdiger

AU - Berger, Ralf

N1 - Funding information: This project was supported by Deutsche Bundesstif-tung Umwelt, DBU, as part of the joint initiative project ‘Biotechnologie in der Lebensmittelindustrie zum produktionsintegrierten Umweltschutz (BIOL)’. We thank E. Hofer of the Centre of Organic Chemistry of the University of Hannover for his help in NMR analyses.

PY - 2005/11

Y1 - 2005/11

N2 - A wild strain of Stemphylium botryosum, when grown submerged in the presence of γ-terpinene (1), yielded the novel highly odour active terpene alcohol (2), whose structure was established by spectroscopic means as p-mentha-1,4-dien-9-ol. During cultivation (2) was further oxidized, predominantly to the corresponding aromatic alcohol p-cymene-9-ol (5). The enantioselective enzymatic introduction of the hydroxyl group at the non-activated C9 of (1) resulted in an enantiomeric excess (ee) of 74% for (2) and 70% for (5), respectively.

AB - A wild strain of Stemphylium botryosum, when grown submerged in the presence of γ-terpinene (1), yielded the novel highly odour active terpene alcohol (2), whose structure was established by spectroscopic means as p-mentha-1,4-dien-9-ol. During cultivation (2) was further oxidized, predominantly to the corresponding aromatic alcohol p-cymene-9-ol (5). The enantioselective enzymatic introduction of the hydroxyl group at the non-activated C9 of (1) resulted in an enantiomeric excess (ee) of 74% for (2) and 70% for (5), respectively.

KW - γ-terpinene

KW - Biotransformation

KW - p-cymene-9-ol

KW - p-mentha-1,4-dien-9-ol

KW - Stemphylium botryosum

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U2 - 10.1080/10242420500444267

DO - 10.1080/10242420500444267

M3 - Article

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VL - 23

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EP - 463

JO - Biocatalysis and biotransformation

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