Studies on the biosynthesis of aliphatic lactones in Sporobolomyces odorus. Conversion of (S)- and (R,S)-13-hydroxy-(Z,E)-9,11-octadecadienoic acid into optically pure (R)-.delta.-decalactone

Albrecht, Wolfgang; Schwarz, Marion; Heidlas, Juergen; Tressl, Roland

doi:10.1021/jo00033a007

Cited by 32 publications

(23 citation statements)

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“…Our results for ␥-C 10 are close to those described by Albrecht et al 5 (the (R) excess of ␥-C 12:1 is 85% against 92% previously reported).…”

Section: Investigation Of the Enantiomeric Composition Of The Lactonessupporting

confidence: 92%

“…In 1992, Albrecht et al 5 reported the enantiomeric ratio of ␥-C 10 (R/S:99/01) and ␥-C 12:1 (R/S:92/08) in one strain of Sporobolomyces odorus (the previous name of Sporidiobolus salmonicolor). However these authors did not give any information about the stability of these ratios during cultivation of the yeast or the impact of the composition of the medium.…”

Section: Sporidiobolus Salmonicolormentioning

confidence: 99%

“…5 Albrecht et al 5 succeeded in the bioconversion of added (E)-3,4-epoxydecanoic acid in ␥-C 10 , but the question is still open. There is a lack of experiments showing the generation of oxygenated precursors in vivo.…”

Section: Hypothesis Of Metabolic Pathways Leading To (R) or (S) ␥-Lacmentioning

confidence: 99%

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Chirality of the ?-lactones produced bySporidiobolus salmonicolor grown in two different media

et al. 1997

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“…Our results for ␥-C 10 are close to those described by Albrecht et al 5 (the (R) excess of ␥-C 12:1 is 85% against 92% previously reported).…”

Section: Investigation Of the Enantiomeric Composition Of The Lactonessupporting

confidence: 92%

Section: Sporidiobolus Salmonicolormentioning

confidence: 99%

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Chirality of the ?-lactones produced bySporidiobolus salmonicolor grown in two different media

et al. 1997

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“…The yeast Sporobolomyces odorus synthesizes decano-5-lactone (1) by the 13-lipoxygenase pathway under inversion of the initial (13S)-configuration into (5R) [18]. Incubation (data not shown) of (13S,9Z,11E)-13-hydroxyoctadeca-9,11-dienoic acid ((13S)-13-HODE) in S. odorus led to (9Z)-13-oxooctadec-9-enoic acid and subsequently to 5-oxodecanoic acid (2c).…”

mentioning

confidence: 99%

Enzymatic Baeyer–Villiger Oxidation as the Key Step in Decano‐4‐lactone and Decano‐5‐lactone Degradation by Sporobolomyces odorus

Garbe

Tressl²

2004

Chemistry & Biodiversity

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The biosyntheses of aroma active gamma- and delta-lactones have been previously characterized in yeasts and plants by incubation of labeled fatty acid derivatives. The lactones were considered as end products. Liquid cultures of the lactone-producing yeast Sporobolomyces odorus were used to investigate catabolic pathways of the lactones by incubation of ethyl (+/-)-5-hydroxy(1-(13)C1)decanoate ((13C)-1b) and methyl (+/-)-4-hydroxy(1-(13)C1)decanoate ((13C)-7a). Aliquots of the culture broth were analyzed with GC/MS after CH2N2 derivatization. S. odorus degraded (13C)-1b to 5-oxo(1-(13)C1)decanoic acid ((13C)-2c) and, subsequently, to pentyl (1-(13)C1)pentanedioate ((13C)-3c) and 3-[(1-(13)C1)carboxypropyl] hexanoate ((13C)-4c) by a Baeyer-Villiger-type oxidation (BVO). In addition, the oxidation of (13C)-7a to 4-oxo(1-(13)C1)decanoic acid ((13C)-8c) and a BVO of (13C)-8c to hexyl (1-(13)C1)butanedioate ((13C)-9c) is reported. So far, BVO has been observed in bacteria and some fungi; the data presented indicate a BVO catalyzed by the yeast S. odorus in the course of endogenous lactone metabolism.

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“…This conclusion can be supported further by the observation that the ability to alter the fatty acid composition of membrane lipids (11,12) Using the above rationale, we chose decane as a typical nontoxic solvent and the transformation of (R)-ricinoleic acid to (R)-y-decalactone catalyzed by a S. ruinenii yeast strain (22) as a model system for our investigation. This particular pathway was selected for the following reasons: (i) the biosynthesis of enantiomerically pure natural lactones has attracted much attention in recent years (23), (ii) the substrate and all the respective intermediates are poorly soluble in water, and (iii) it had been previously demonstrated with several microorganisms that stepwise B3-elimination of hydroxy-acids was a general mechanism responsible for the formation of lactones (23,24 Fig. 2, the addition of (R)-ricinoleic acid (compound 1) led to the accumulation of some additional compounds in the organic phase (labeled in Figs.…”

mentioning

confidence: 99%

Analysis of metabolic pathways by the growth of cells in the presence of organic solvents.

Spinnler

Giniès

Khan

et al. 1996

Proc. Natl. Acad. Sci. U.S.A.

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A new approach to the analysis of metabolic pathways involving poorly water-soluble intermediates is proposed. It (2 g), KH2PO4 (2 g), CaCl2 (0.13 g), FeSO4 (0.01 g), MgSO4 (3 g), and Tween 80 (2 g) were added to distilled water (1 liter), and the pH was adjusted to 6 with 2 M NaOH. One hundred milliliters of this medium was inoculated with a 1% subculture in 250-ml flasks (previously sterilized at 121°C for 20 min). The cultures were then incubated at 25°C with orbital agitation (200 rpm).The number of viable cells was determined by counting the number of colonies formed after 5 days on Petri dishes containing malt agar medium. The inoculum consisted of 0.1 ml of a suitable dilution of the cultures in water containing 1% peptone. The specific growth rate (,u) was calculated on the basis of colony-forming units per hour. GC and GC-MS Analyses. GC and GC-MS analyses were performed using HP 5890 GC and HPMSD 5970 GC-MS instruments with an HP1 column (1200 x 0.020 cm; film thickness = 0.33 ,um) and using helium as a carrier gas at a linear flow rate of 35 cm/s. The injector temperature was set to 250°C, and the interface was at 280°C. The oven temperature was programmed from 80-250°C at 4°C per min. The electronic impact energy was set at 70 eV, and data were collected in the range of 72-500 atomic mass units. For sample preparation, the culture suspension was centrifuged (4000 rpm for 3 min) and a 2-ml portion of the decane layer was dried prior to silylation with 100 gul of 50% (wt/vol) bis(trimethylsilyl)trifluoroacetamide (BSTFA) in pyridine.

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Studies on the biosynthesis of aliphatic lactones in Sporobolomyces odorus. Conversion of (S)- and (R,S)-13-hydroxy-(Z,E)-9,11-octadecadienoic acid into optically pure (R)-.delta.-decalactone

Cited by 32 publications

References 0 publications

Chirality of the ?-lactones produced bySporidiobolus salmonicolor grown in two different media

Chirality of the ?-lactones produced bySporidiobolus salmonicolor grown in two different media

Enzymatic Baeyer–Villiger Oxidation as the Key Step in Decano‐4‐lactone and Decano‐5‐lactone Degradation by Sporobolomyces odorus

Analysis of metabolic pathways by the growth of cells in the presence of organic solvents.

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