Stereochemistry of the biogeneration of C-10 and C-12 gamma lactones inYarrowia lipolytica andPichia ohmeri

Ercoli, Barbara; Fuganti, Claudio; Grasselli, Piero; Servi, Stefano De; Allegrone, Gianna; Barbeni, Massimo; Pisciotta, Antonella

doi:10.1007/bf01021639

Cited by 22 publications

(21 citation statements)

References 7 publications

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“…We can however mention that the stereochemistry of the lactone-generating reactions is an intrinsic parameter for each species. Ercoli et al (1992) thus observed, when growing Y. lipolytica or P. ohmeri on the same racemic hydroxy acids, that the two species produced the opposite enantiomers.…”

Section: Peroxisomal B-oxidationmentioning

confidence: 78%

Catabolism of hydroxyacids and biotechnological production of lactones by Yarrowia lipolytica

Waché¹,

Aguedo²,

Nicaud

et al. 2003

Appl Microbiol Biotechnol

116

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The g-and d-lactones of less than 12 carbons constitute a group of compounds of great interest to the flavour industry. It is possible to produce some of these lactones through biotechnology. For instance, g-decalactone can be obtained by biotransformation of methyl ricinoleate. Among the organisms used for this bioproduction, Yarrowia lipolytica is a yeast of choice. It is well adapted to growth on hydrophobic substrates, thanks to its efficient and numerous lipases, cytochrome P450, acylCoA oxidases and its ability to produce biosurfactants. Furthermore, genetic tools have been developed for its study. This review deals with the production of lactones by Y. lipolytica with special emphasis on the biotransformation of methyl ricinoleate to g-decalactone. When appropriate, information from the lipid metabolism of other yeast species is presented.

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Section: Peroxisomal B-oxidationmentioning

confidence: 78%

Catabolism of hydroxyacids and biotechnological production of lactones by Yarrowia lipolytica

Waché¹,

Aguedo²,

Nicaud

et al. 2003

Appl Microbiol Biotechnol

116

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“…4-dodecanolide is obtained in the (S) enantiomeric form from Yarrowia lipolytica, whereas the opposite (R) enantiomer is present among the metabolites of Pichia ohmeri. 8 Fusarium poae produced (6Z)-dodecen-4-olide only in the (R) form, suggesting that the precursor exists exclusively in the (R) form whereas 4-dodecanolide and 4-decanolide were present in an enantiomers mixture.…”

Section: Determination Of Enantiomeric Compositionmentioning

confidence: 96%

“…It was proven that the precursors of lactones were hydroxylated fatty acids of C18 chain length, which were shortened by ␤-oxidation steps followed by lactonization. 8,15,21 Haffner and Tressel 15 have studied the biotransformation of oleic acid to ␥ C10, C12 saturated and unsaturated lactones in Sporobolomyces odorus. They concluded that at least three different metabolic pathways were used for the first step including action of 10-hydratase and/or 10 lipoxygenase for C12 lactone formation.…”

Section: Determination Of Enantiomeric Compositionmentioning

confidence: 99%

“…Although several lactones have been reported as primary or secondary metabolites of microorganisms, the intervention of Penicillium roqueforti in the formation of lactones in milk products has never been reported so far. [4][5][6][7][8] According to the stereoselectivity of enzymatic reactions involved in their biosynthesis, biological compounds occur in a pure enantiomeric form or in a predominant form. Also, determination of enantiomeric purity is generally used as a criterion of the ''natural'' origin of the aroma compounds.…”

mentioning

confidence: 99%

“…However, in most cases, (R)-␥-lactones are found as the dominating enantiomer, whereas a variation of (R/S) ratios of lactone enantiomers was revealed during production of lactones by different microorganisms. 7,8,[12][13][14][15] On the other hand, chiral analysis of the lactones obtained during the microbial conversion of fatty acids provides complementary information on the biosynthetic pathways involved. 8,14,15 This paper reports the study of the chirality of ␥-lactones produced during the microbial conversion of soy bean fatty acids by Penicillium roqueforti spores in the presence of lipase MY.…”

mentioning

confidence: 99%

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Enantiodifferentiation of four ?-lactones produced byPenicillium Roqueforti

Chalier

Crouzet

1998

Chirality

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Expression of vitreoscilla hemoglobin improves growth and levels of extracellular enzyme in yarrowia lipolytica

Bhave

Chattoo

2003

Biotech & Bioengineering

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Enhancement in oxygen uptake by high-celldensity cultivations has been achieved previously by expression of the bacterial hemoglobin gene from Vitreoscilla. The Vitreoscilla hemoglobin (VHb) gene was expressed in the yeast Yarrowia lipolytica to study the effect of expression in this commercially important yeast. The expression of VHb in this yeast was found to enhance growth, contrary to reported observations in wild-type Saccharomyces cerevisiae in which there was no significant growth enhancement. VHb-expressing Y. lipolytica exhibited higher specific growth rate, enhanced oxygen uptake rate, and higher respiratory activity. We report the beneficial effects of VHb expression on growth under microaerobic as well as under nonlimiting dissolved oxygen conditions. Earlier studies in Y. lipolytica have demonstrated inhibition of mycelia formation by respiratory inhibitors and poor nitrogen source, conditions poor for growth. VHb + Y. lipolytica cells were more efficient at forming mycelia, indicating better utilization of available oxygen as compared with the VHb À cells. Expression of VHb was also found to increase the levels of enzyme ribonuclease secreted into the medium, a property that may be beneficial for producing heterologous proteins in Y. lipolytica. B

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Stereochemistry of the biogeneration of C-10 and C-12 gamma lactones inYarrowia lipolytica andPichia ohmeri

Cited by 22 publications

References 7 publications

Catabolism of hydroxyacids and biotechnological production of lactones by Yarrowia lipolytica

Catabolism of hydroxyacids and biotechnological production of lactones by Yarrowia lipolytica

Enantiodifferentiation of four ?-lactones produced byPenicillium Roqueforti

Expression of vitreoscilla hemoglobin improves growth and levels of extracellular enzyme in yarrowia lipolytica

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