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Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
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Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.
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The conversion of allylic alcohols into epoxides using the chiral catalyst was discovered by K. Barry Sharpless and is known as Sharpless epoxidation. The use of a chiral catalyst enables the formation of one enantiomer of the product in excess. This chiral catalyst is mainly a chiral complex of titanium tetraisopropoxide and tartrate ester (specific stereoisomer). The stereoisomer used in the chiral catalyst dictates the formation of the enantiomer of the product. In other words, the use of...
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Efficient Production of 4'-Hydroxydihydrochalcones Using Non-Conventional Yeast Strains.

Paweł Chlipała1, Julia Bienia1, Marcelina Mazur1

  • 1Department of Food Chemistry and Biocatalysis, Faculty of Biotechnology and Food Science, Wrocław University of Environmental and Life Sciences, 50-375 Wrocław, Poland.

International Journal of Molecular Sciences
|October 16, 2024
PubMed
Summary

Novel yeast strains efficiently produce 4-hydroxydihydrochalcones from natural products. This biotransformation method offers a sustainable route to valuable compounds for therapeutic and nutraceutical applications.

Keywords:
biotransformationchalconedihydrochalconeshydrogenationnatural productsnon-conventional yeasts

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Area of Science:

  • Biotechnology
  • Natural Products Chemistry
  • Microbiology

Background:

  • Natural products are a key source for novel therapeutic agents.
  • Dihydrochalcones possess diverse pharmacological properties.
  • Dragon's blood resin contains valuable chalcones but is challenging to isolate.

Purpose of the Study:

  • To investigate efficient production of 4'-hydroxydihydrochalcones using non-conventional yeast.
  • To evaluate biotransformation efficiency of various 4'-hydroxychalcone substrates.
  • To explore yeast-catalyzed production of dihydrochalcones for therapeutic and nutraceutical development.

Main Methods:

  • Screening of yeast strains including *Yarrowia lipolytica*, *Saccharomyces cerevisiae*, *Rhodotorula rubra*, and *Rhodotorula glutinis*.
  • Biotransformation assays using various 4'-hydroxychalcone substrates.
  • Analysis of conversion efficiencies and influence of methoxy substituents on hydrogenation.

Main Results:

  • Selected yeast strains (*Y. lipolytica* KCh 71, *R. rubra* KCh 4 & KCh 82, *R. glutinis* KCh 242) showed high conversion efficiencies (>98% in 1 hour).
  • Methoxy substituent position on the chalcone ring impacted hydrogenation efficiency.
  • Light exposure induced isomerization of *trans*-4'-hydroxy-2-methoxychalcone to its *cis* isomer.

Conclusions:

  • Yeast strains offer a sustainable and efficient method for dihydrochalcone production.
  • This biotransformation approach facilitates the development of new therapeutic agents and nutraceuticals.
  • Understanding substrate specificity and reaction conditions is crucial for optimizing dihydrochalcone synthesis.