Biotransformation of (+)-carvone and (−)-carvone using human skin fungi: A green method of obtaining fragrances and flavours

Santos, Rogério Aparecido Minini dos; Souza, Felipe de Oliveira; Pilau, Eduardo Jorge; Porto, Carla; Gonçalves, José Eduardo; Oliveira, Arildo José Braz de; Gonçalves, Regina Aparecida Correia

doi:10.1080/10242422.2017.1376049

Cited by 11 publications

(5 citation statements)

References 18 publications

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“…The application of bacterial whole-cell biocatalysts for this reduction reaction was already demonstrated to be beneficial in comparison to other microorganisms, since conversions of ≥96% were reached whereas the undesired reduction of carbonyl bonds by endogenous carbonyl reductases was not observed [19,22,23]. The reduction of the C=O bonds of substrate or product was mostly an issue when applying other organisms like yeasts [18,24,25] and other fungi [24,26], plant cells [27], or microalgae [28].…”

Section: Discussionmentioning

confidence: 99%

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Asymmetric Whole-Cell Bio-Reductions of (R)-Carvone Using Optimized Ene Reductases

et al. 2019

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(2R,5R)-dihydrocarvone is an industrially applied building block that can be synthesized by site-selective and stereo-selective C=C bond bio-reduction of (R)-carvone. Escherichia coli (E. coli) cells overexpressing an ene reductase from Nostoc sp. PCC7120 (NostocER1) in combination with a cosubstrate regeneration system proved to be very effective biocatalysts for this reaction. However, the industrial applicability of biocatalysts is strongly linked to the catalysts’ activity. Since the cell-internal NADH concentrations are around 20-fold higher than the NADPH concentrations, we produced E. coli cells where the NADPH-preferring NostocER1 was exchanged with three different NADH-accepting NostocER1 mutants. These E. coli whole-cell biocatalysts were used in batch operated stirred-tank reactors on a 0.7 l-scale for the reduction of 300 mM (R)-carvone. 287 mM (2R,5R)-dihydrocarvone were formed within 5 h with a diasteromeric excess of 95.4% and a yield of 95.6%. Thus, the whole-cell biocatalysts were strongly improved by using NADH-accepting enzymes, resulting in an up to 2.1-fold increased initial product formation rate leading to a 1.8-fold increased space-time yield when compared to literature.

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Section: Discussionmentioning

confidence: 99%

“…The bio-reduction of ( R )-carvone has already been studied using many different microorganisms, including bacteria [19,23], yeasts [18,24,25], other fungi [24,26], plant cells [27], or microalgae [28]. With more than 30 different strains, yeasts and yeast-like fungi are the largest group studied for this reaction [18,24,25].…”

Section: Discussionmentioning

confidence: 99%

Asymmetric Whole-Cell Bio-Reductions of (R)-Carvone Using Optimized Ene Reductases

et al. 2019

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“…Biocatalysis typically displays specific stereoreferences, therefore multiple studies have reported the use of whole-cell or isolated enzyme catalysts for dihydrocarvone synthesis (Table ). In the early stages, fungi (such as yeast and mushrooms), − plant cells (such as moss and marine microalgae) , and bacteria were carried out for the biotransformation from (5 R )- or (5 S )-carvone to dihydro products. However, the conversion and stereoselectivity show significant differences due to different biocatalysts.…”

Section: Terpenoid Flavormentioning

confidence: 99%

Applications of Ene-Reductases in the Synthesis of Flavors and Fragrances

Fan,

Yu,

Yao

et al. 2024

J. Agric. Food Chem.

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Flavors and fragrances (F&F) are interesting organic compounds in chemistry. These compounds are widely used in the food, cosmetic, and medical industries. Enzymatic synthesis exhibits several advantages over natural extraction and chemical preparation, including a high yield, stable quality, mildness, and environmental friendliness. To date, many oxidoreductases and hydrolases have been used to biosynthesize F&F. Ene-reductases (ERs) are a class of biocatalysts that can catalyze the asymmetric reduction of α,β-unsaturated compounds and offer superior specificity and selectivity; therefore, ERs have been increasingly considered an ideal alternative to their chemical counterparts. This review summarizes the research progress on the use of ERs in F&F synthesis over the past 20 years, including the achievements of various scholars, the differences and similarities among the findings, and the discussions of future research trends related to ERs. We hope this review can inspire researchers to promote the development of biotechnology in the F&F industry.

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“…Biodiesel consists of mono-alkyl esters derived from longchain fatty acids originating from plants. One of the potential natural resources for the development of biodiesel in Indonesia is crude palm oil (CPO) (dos Santos et al, 2018;Usman et al, 2019).…”

Section: Introductionmentioning

confidence: 99%

“…Generally, two reaction steps could be used to synthesize biodiesel from CPO based on differences in FFA levels. These reactions include a transesterification reaction using an alkaline catalyst for CPO with an FFA of less than 5% and an esterification reaction using an acid catalyst for CPO with an FFA of more than 5% (dos Santos et al, 2018;Peter et al, 2021). In addition, esterification and transesterification can be carried out simultaneously using a catalyst that has both acidic and basic sites (Usman et al, 2019).…”

Section: Introductionmentioning

confidence: 99%

Determination of Optimum Conditions for Synthesis of Methyl Ester from Bleached Crude Palm Oil Using Sn-Zeolite and Red Mud Catalysts

Amelyanti,

Usman,

Rahmalia

2023

J. Presipitasi

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Methyl esters synthesis from bleached crude palm oil (BCPO) containing 0.36 and 20.86% of free fatty acids using Sn-zeolite and red mud has been done. This study aims to determine the esterification, transesterification, and transesterification-esterification simultaneous reactions optimum conditions when using Sn-zeolite, red mud, and Sn-zeolite-red mud mixture catalysts. The X-ray diffraction and Fourier transform infrared analysis results show that Sn has been impregnated on zeolite, indicated by cassiterite and Sn-O-Sn vibrational peaks in Sn-zeolite. The main component of red mud is NaCO3, indicated by analcite and carbonate peaks. Thin-layer chromatography results in the transesterification showed that red mud catalyst could totally convert triglycerides from BCPO to methyl ester when 5% catalyst, 3 hours, and CPO:methanol mole ratio 1:20 were used. In esterification, Sn-zeolite can synthesize methyl ester from low-quality CPO when using CPO:methanol mole ratio 1:20 for 3 hours, however, the conversion was not total. In the transesterification-esterification simultaneous, the conversion was also not total which the best reaction conditions at mixing Sn-zeolite:red mud 1.5:1 (w/w), 7% catalyst, and CPO:methanol mole ratio 1:20 for 3 hours. This study shows that esterification and transesterification processes can be carried out simultaneously at a particular mass ratio of Sn-zeolite and red mud.

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Biotransformation of (+)-carvone and (−)-carvone using human skin fungi: A green method of obtaining fragrances and flavours

Cited by 11 publications

References 18 publications

Asymmetric Whole-Cell Bio-Reductions of (R)-Carvone Using Optimized Ene Reductases

Asymmetric Whole-Cell Bio-Reductions of (R)-Carvone Using Optimized Ene Reductases

Applications of Ene-Reductases in the Synthesis of Flavors and Fragrances

Determination of Optimum Conditions for Synthesis of Methyl Ester from Bleached Crude Palm Oil Using Sn-Zeolite and Red Mud Catalysts

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