Use of<i>Saccharomyces cerevisiae</i>Yeasts in the Chemoselective Bioreduction of (1E,4E)-1,5-Bis(4-Methoxyphenyl)-1,4-Pentadien-3-one in Biphasic System

Schaefer, César A.; Silva, Vanessa D.; Stambuk, Boris U.; Nascimento, Maria da Graça

doi:10.5935/0103-5053.20130140

Cited by 3 publications

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“…However, in the case of single-step biotransformation, isolated enzymes can be considered as a better choice and can be used as a free or immobilized biocatalyst either in aqueous or organic media [63]. Yeasts, especially Saccharomyces species, are primarily known from whole cell reductive activity [64,65] and are used in the food industry for the production of alcoholic beverages as well as for bread fermentation [3]. However, yeasts are a source of enzymes such as: lipases, dehydrogenases, or invertase.…”

Section: Yeast's Enzymes Applicationsmentioning

confidence: 99%

Yeast as a Versatile Tool in Biotechnology

Żymańczyk–Duda¹,

Brzezińska-Rodak²,

MagdalenaKlimek-Ochab³

et al. 2017

Yeast - Industrial Applications

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Yeasts represent a very diverse group of microorganisms, and even strains that are classified as the same species often show a high level of genetic divergence. Yeasts biodiversity is closely related to their applicability. Biotechnological importance of yeast is almost immeasurable. For centuries, people have exploited its enzymatic potential to produce fermented food as bread or alcoholic beverages. Admittedly, yeasts application was initially instinctual, but with science and technology development, these microorganisms got the object of thorough scientific investigations. It must be recognized that yeast represents an excellent scientific model because of its eukaryotic origin and knowledge of genetics of yeast cells as well as metabolism examined in detail. In 1996, the genome of baker yeast Saccharomyces cerevisiae has been elucidated, what opened the opportunity for the global study of the expression and functioning of the eukaryotic genome. Also, currently, an international team is working on the synthesis of the 16 yeast chromosomes by synthetic biology tools, and the results are expected till the end of the year. Nowadays, yeast is regarded as a versatile tool for biotechnological purposes.

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Section: Yeast's Enzymes Applicationsmentioning

confidence: 99%

Yeast as a Versatile Tool in Biotechnology

Żymańczyk–Duda¹,

Brzezińska-Rodak²,

MagdalenaKlimek-Ochab³

et al. 2017

Yeast - Industrial Applications

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“…Uma vez que estes métodos empregam metais de elevados custos e que são finitos na natureza, os métodos enzimáticos estão sendo desenvolvidos a fim de serem uma alternativa viável para a redução desta classe de compostos[70],[71] e[72]. estruturas pró quirais, sendo assim ao reduzi-los, o produto será quiral e é possível obter excessos enantioméricos devido a estereoespecificidade das enzimas presentes no fungo.Assim, este trabalho foi norteado pela síntese de adutos de Knoevenagel e suas possíveis aplicações utilizando metodologias com protocolos sustentáveis.…”

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Síntese de adutos de Knoevenagel e de <i>4H</i> cromenos por irradiação micro-ondas e reações de biotransformação

Zanin¹

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Dedico este trabalho ao meu pai Valcenir Aparecido Zanin, minha mãe Vera Lúcia de Oliveira Lima Zanin, ao meu irmão Guilherme Lima Zanin e a minha avó Elvira de Oliveira Lima, por estarem sempre ao meu lado me apoiando, com muito amor, em todos meus passos durante toda minha vida. A Giovanna, pelo companheirismo, paciência, amor, carinho e apoio durante esses dois anos de mestrado, me incentivando a lutar sempre pelos meus objetivos. Ao Prof. Dr. André Luiz Meleiro Porto, pelos dois anos de orientação, paciência, amizade e ensinamentos que foram fundamentais na minha formação pessoal e profissional.

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Biorredução de compostos carbonílicos alfa,beta-insaturados visando à síntese de substâncias opticamente ativas

Silva¹

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Palavras-chave: Biorredução, compostos carbonílicos α,β-insaturados, micro-organismo, Saccharomyces cerevisiae. In recent years, the preparation of enantiomerically pure compounds has become a concern and a challenge to the industry. This fact is a consequence of the tenuous relationship between the spatial structure of substances and the different flavors, odors, pharmacokinetic and pharmacodynamic processes and toxicity that they play in the body. In this context, the asymmetric synthesis of α-alkyl substituted optically active carbonyl compounds has received great attention because they are important building blocks in the synthesis of chiral drugs and natural products. Thus, this study aimed to develop methodologies that allow the preparation of this enantiomerically pure compounds by controlling the formation of stereogenic centers using biocatalysis. To this end, various activated olefins substituted with electron withdrawing groups (carbonyl) were synthesized using two procedures, aldol condensation and esterification reactions. These α,β-unsaturated carbonyl compounds were obtained in good yields (48-94%) and subjected to the biocatalytic reduction mediated by whole cells of microorganisms. Initially, we used the olefin (E)-3-methyl-4-phenyl-3-buten-2-one (51a) as a model substrate for the optimization of the experimental conditions and determine wich one provide the product with better conversion and enantiomeric purity. In these tests, we evaluated various reaction parameters such as the composition of the reaction medium (aqueous, biphasic and buffer), the presence of additives (glucose and phase transfer catalyst), different microorganisms and adsorbing effect of using Amberlite XAD-7. Thus, the biorreduction in aqueous medium, without additives, mediated by LSC-II yeast and with the application of Amberlite XAD-7 was the reaction condition that presented the best enantiomeric excess (81%) and was selected for a methodological study that evaluated the steric and electronic effects of the substituents. It was observed that the substituent in the β-position of the aryl group, the size increase of the α-substituent and the presence of an ester group had an important role in the stereoselectivity of the reaction. Finally, application of the methodology on muguesia enantioselective synthesis, a floral fragrance, was evaluated. The results obtained showed the high potential of the methodology in chemoselective bioreduction of α,β-unsaturated carbonyl compounds and preparation of optically active substances.

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Use ofSaccharomyces cerevisiaeYeasts in the Chemoselective Bioreduction of (1E,4E)-1,5-Bis(4-Methoxyphenyl)-1,4-Pentadien-3-one in Biphasic System

Cited by 3 publications

References 0 publications

Yeast as a Versatile Tool in Biotechnology

Yeast as a Versatile Tool in Biotechnology

Síntese de adutos de Knoevenagel e de <i>4H</i> cromenos por irradiação micro-ondas e reações de biotransformação

Biorredução de compostos carbonílicos alfa,beta-insaturados visando à síntese de substâncias opticamente ativas

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