Enantioselective hydrolyses with Yarrowia lipolytica: a versatile strain for esters, enol esters, epoxides, and lactones

Fantin, Giancarlo; Fogagnolo, Marco; Guerrini, Alessandra; Medici, Alessandro; Pedrini, Paola; Fontana, Silvia

doi:10.1016/s0957-4166(01)00463-3

Cited by 20 publications

(14 citation statements)

References 28 publications

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“…The compounds detected during the pathway were first those accumulating between two b-oxidation loops (Okui et al 1963a), excluding the 4-hydroxydecanoic acid which was probably lactonising spontaneously before detection, as reported for other 4-hydroxy acids (Fantin et al 2001). This very unstable acid was later detected (Feron et al 1996) and the detection of other intermediates was improved with the use of biphasic media or by processing the pathway in vitro (Blin-Perrin et al 2000).…”

Section: Peroxisomal B-oxidationmentioning

confidence: 87%

“…This suggests that the step of hydrolysis of the lactone exhibits a high control on the degradation. Then, the specificity of the degradation pathway is high, as degradation resolves the racemic (Fuganti et al 1993;Latrasse et al 1993;Fantin et al 2001) and no degradation has been observed in the same conditions for closely related lactones, such as hydroxy-g-decalactone or decen-4-olides (WachØ et al 2001). Several pathways of degradation are possible.…”

Section: Lactone Degradationmentioning

confidence: 99%

See 1 more Smart Citation

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: 87%

Section: Lactone Degradationmentioning

confidence: 99%

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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“…Despite this limitation, whole-cell biotransformation was shown to be efficient Lee et al, 2004). A low level of EH activity has been reported towards styrene oxide in another wild-type Y. lipolytica strain (Fantin et al, 2001). However, no EH activity could be detected in Y. lipolytica strains derived from the W29 wild-type strain, including Po1h, for the substrate evaluated in the present study.…”

Section: Discussionmentioning

confidence: 49%

Cloning of an epoxide hydrolase‐encoding gene from Rhodotorula mucilaginosa and functional expression in Yarrowia lipolytica

Labuschagne

Albertyn

2006

Yeast

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Epoxide hydrolases (EHs), especially those of fungal origin, have the ability to catalyse the enantioselective hydrolysis of epoxides to their corresponding diols. Recombinant DNA technology has been used extensively to overproduce these catalysts for the efficient hydrolytic kinetic resolution of epoxides, which serve as high-value intermediates in the fine chemicals and pharmaceutical industries. Degenerate primers, based on data from available EH-encoding gene sequences, in conjunction with inverse PCR, were used to amplify the genomic EH-encoding gene from Rhodotorula mucilaginosa. The 2347 bp genomic sequence revealed a 1979 bp ORF containing nine introns. The cDNA sequence revealed an 1185 bp EH-encoding gene that translates into a 394 amino acid protein exhibiting low sequence homology towards the known EH proteins. The EH gene from R. mucilaginosa was functionally expressed in Yarrowia lipolytica using a constitutive integrative expression cassette. Whole-cell biotransformation of (2,3-epoxypropyl)benzene, using the recombinant EH, revealed activity and selectivity far superior to any other activity and selectivity reported in literature using wild-type organisms. The GenBank Accession No. for the R. mucilaginosa EH gene is AY627310.

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“…Whole cells of Y. lipolytica were shown to carry out enantioselective hydrolysis of a range of racemic acetyl esters of secondary alcohols as well as enol esters (Fantin et al, 2001 ). As for ketones and alcohols, these authors demonstrated that the yields, enantiomeric excesses and enantioselectivity varied depending on the strain and the substrates.…”

Section: Resolution Of Estersmentioning

confidence: 99%

Applications of the Non-Conventional Yeast Yarrowia lipolytica

Nicaud

Gaillardin

2009

Yeast Biotechnology: Diversity and Applications

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Enantioselective hydrolyses with Yarrowia lipolytica: a versatile strain for esters, enol esters, epoxides, and lactones

Cited by 20 publications

References 28 publications

Catabolism of hydroxyacids and biotechnological production of lactones by Yarrowia lipolytica

Catabolism of hydroxyacids and biotechnological production of lactones by Yarrowia lipolytica

Cloning of an epoxide hydrolase‐encoding gene from Rhodotorula mucilaginosa and functional expression in Yarrowia lipolytica

Applications of the Non-Conventional Yeast Yarrowia lipolytica

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