Fungi isolated from food samples for an efficient stereoselective production of phenylethanols

Decarlini, María Florencia; Aimar, Mario L.; Vázquez, Ana María; Vero, Silvana; Rossi, L.; Yang, Pablo

doi:10.1016/j.bcab.2017.10.014

Cited by 14 publications

(8 citation statements)

References 49 publications

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“…The methodology used was the same as that described in the previous section, but the racemic mixtures of substituted (R,S)-1-PE (50 mg) described in Table 1 were used as substrates. The valuation and identification of the obtained products was carried out as described by Decarlini et al (2017).…”

Section: Calculation Methods For Determinations By Gcmentioning

confidence: 99%

“…Acetophenone (AP) and NaBH 4 were purchased from Sigma-Aldrich S.A. (Argentina), and (S)-1phenylethanol ((S)-1-PE) and (R)-1-phenylethanol ((R)-1-PE) were synthesized using methodologies reported in the literature (Aimar et al, 2014;Decarlini et al, 2017)…”

Section: Generalmentioning

confidence: 99%

“…Retention times of AP, (S)-1-PE and (R)-1-PE were 14.28, 19.77, and 20.41 min, respectively. The identities of the peaks of the enantiomers in the chromatogram were established using pure (S)-1-PE and (R)-1-PE as reference standards (Aimar et al, 2014;Decarlini et al, 2017). In addition, the elution order and retention times of the GC data were compared with those reported in the literature for the same column (Orden et al, 2009).…”

Section: Gc-fid and Gc-ms Analysesmentioning

confidence: 99%

“…We recently reported the stereoselective reduction of acetophenones and its derivatives using a strain of Galactomyces candidus isolated from a decaying carrot (Decarlini et al, 2017). The performance of the reduction system was shown to be extremely efficient (>99.9 e.e.%) for some substituted acetophenones, and the substrate specificity of the system was also very good.…”

Section: Introductionmentioning

confidence: 99%

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Kinetic profiles of the stereoselective reduction of acetophenone and its derivatives promoted by Galactomyces candidus GZ1. A mechanistic interpretation

Decarlini

Bordón

Vázquez

et al. 2019

Biocatalysis and Agricultural Biotechnology

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Section: Calculation Methods For Determinations By Gcmentioning

confidence: 99%

Section: Generalmentioning

confidence: 99%

Section: Gc-fid and Gc-ms Analysesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Kinetic profiles of the stereoselective reduction of acetophenone and its derivatives promoted by Galactomyces candidus GZ1. A mechanistic interpretation

Decarlini

Bordón

Vázquez

et al. 2019

Biocatalysis and Agricultural Biotechnology

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“…Chemoenzymatic synthesis of enantiopure (S)-(−)-Rivastigmine [19][20][21][22][23] or (R)-(−)-Phenylephrine [24][25][26][27] has been performed with multipathway processes involving asymmetric transformations of 3-hydroxyacetophenone to optically active corresponding esters. Lipase-catalyzed kinetic resolution for the production of enantiomerically pure alcohols precursors is a less described path.…”

Section: Introductionmentioning

confidence: 99%

Efficient access to both enantiomers of 3‐(1‐hydroxyethyl)phenol by regioselective and enantioselective CAL‐B–catalyzed hydrolysis of diacetate in organic media by sodium carbonate

2018

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In the present paper, we describe several pathways employing immobilized lipase from Candida antarctica B (CAL‐B) as biocatalyst to prepare easily both enantiomers of 3‐(1‐hydroxyethyl)phenol. We have applied hydrolysis with Na2CO3 in organic media under mild conditions. The reaction parameters solvent effect, amount of lipase, and Na2CO3 were examined with 3‐(1‐acetoxyethyl)phenyl acetate as substrate. In alkaline hydrolysis, (R)‐3‐(1‐hydroxyethyl)phenol was obtained with ee = 99% and (S)‐(−)‐3‐(1‐acetoxyethyl)phenol with ee = 98% at optimal conversion (c = 50%) and high selectivity (E > 200). Two other deacylation reactions were compared: alcoholysis with MeOH and with NEt3. The acylation of 3‐(1‐hydroxyethyl)phenol with vinyl acetate was also examined. Alkaline hydrolysis gave the best results, while good regioselectivity and enantioselectivity were observed in alcoholysis and acylation reactions. Finally, (S)‐ and (R)‐3‐(1‐hydroxyethyl)phenol (ee > 98%), key intermediates for the synthesis of important drugs, were prepared from the corresponding racemic diacetate through alkaline hydrolysis.

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Comparing the Catalytic and Structural Characteristics of a ‘Short’ Unspecific Peroxygenase (UPO) Expressed in Pichia pastoris and Escherichia coli

et al. 2022

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Unspecific peroxygenases (UPOs) have emerged as valuable tools for the oxygenation of non-activated carbon atoms, as they exhibit high turnovers, good stability and depend only on hydrogen peroxide as the external oxidant for activity. However, the isolation of UPOs from their natural fungal sources remains a barrier to wider application. We have cloned the gene encoding an 'artificial' peroxygenase (artUPO), close in sequence to the 'short' UPO from Marasmius rotula (MroUPO), and expressed it in both the yeast Pichia pastoris and E. coli to compare the catalytic and structural characteristics of the enzymes produced in each system. Catalytic efficiency for the UPO substrate 5-nitro-1,3-benzodioxole (NBD) was largely the same for both enzymes, and the structures also revealed few differences apart from the expected glycosylation of the yeast enzyme. However, the glycosylated enzyme displayed greater stability, as determined by nano differential scanning fluorimetry (nano-DSF) measurements. Interestingly, while artUPO hydroxylated ethylbenzene derivatives to give the (R)-alcohols, also given by a variant of the 'long' UPO from Agrocybe aegerita (AaeUPO), it gave the opposite (S)-series of sulfoxide products from a range of sulfide substrates, broadening the scope for application of the enzymes. The structures of artUPO reveal substantial differences to that of AaeUPO, and provide a platform for investigating the distinctive activity of this and related'short' UPOs.

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Fungi isolated from food samples for an efficient stereoselective production of phenylethanols

Cited by 14 publications

References 49 publications

Kinetic profiles of the stereoselective reduction of acetophenone and its derivatives promoted by Galactomyces candidus GZ1. A mechanistic interpretation

Kinetic profiles of the stereoselective reduction of acetophenone and its derivatives promoted by Galactomyces candidus GZ1. A mechanistic interpretation

Efficient access to both enantiomers of 3‐(1‐hydroxyethyl)phenol by regioselective and enantioselective CAL‐B–catalyzed hydrolysis of diacetate in organic media by sodium carbonate

Comparing the Catalytic and Structural Characteristics of a ‘Short’ Unspecific Peroxygenase (UPO) Expressed in Pichia pastoris and Escherichia coli

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