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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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Replacing each alpha-hydrogen in chloroethane by bromine (or a different functional group) yields a pair of enantiomers. Such protons are called prochiral or enantiotopic and are related by a mirror plane. Enantiotopic protons are chemically equivalent in an achiral environment. Because most proton NMR spectra are recorded using achiral solvents, enantiotopic hydrogens yield a single signal.
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Enols are a class of compounds where a hydroxyl group is attached to a carbon–carbon double bond, which implies that it is a vinyl alcohol. A carbonyl compound with an α hydrogen undergoes keto–enol tautomerism and remains in equilibrium with its tautomer, the enol form. Usually, the keto tautomer is present in a higher concentration than the enol tautomer due to the higher bond energy of C=O compared to C=C. Moreover, the direction of the keto–enol equilibrium is...
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As depicted in the figure below, the unsymmetrical ketones can form two possible enolates:  less substituted or more substituted enolates. Usually, the thermodynamic enolates are formed from the more substituted α-carbon atom, while the kinetic enolates are formed faster by deprotonation from the less substituted position. The thermodynamic enolates have lower energy, so they are  more stable. But the energy required to form kinetic enolates is less.
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Studies in enantioselective microbial deuteration.

Carl Recsei1, Marina Cagnes1, Robert A Russell1

  • 1Australian Nuclear Science and Technology Organisation, National Deuteration Facility, New Illawarra Rd, Lucas Heights, New South Wales, 2234, Australia. recseic@ansto.gov.au.

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This study presents cost-effective microbial deuteration methods achieving over 95% isotopic labeling for chiral building blocks. Novel yeast strains and methanol-d4 enable efficient deuterium incorporation for medicinal and analytical applications.

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Area of Science:

  • Biocatalysis and Isotope Labeling
  • Synthetic Organic Chemistry
  • Microbial Biotechnology

Background:

  • Deuterium-labeled compounds are crucial for medicinal and analytical applications.
  • Current methods for achieving high levels of isotopic labeling can be expensive and complex.
  • Exploring diverse microbial resources offers potential for more economical isotope labeling strategies.

Purpose of the Study:

  • To develop economical methods for reductive microbial deuteration with high isotopic labeling.
  • To evaluate various yeast strains and inexpensive carbon sources for deuterium incorporation.
  • To assess the utility of molecular rotational resonance spectroscopy for process evaluation.

Main Methods:

  • Utilized a strategy of alpha-hydrogen exchange followed by microbial reduction for deuteration.
  • Employed specific yeast strains like Saccharomyces cerevisiae MBG5177 and Pichia pastoris X-33.
  • Used methanol-d4 as an affordable deuterated carbon source.
  • Applied molecular rotational resonance spectroscopy (MRR) for analysis of deuteration levels and enantiopurity.

Main Results:

  • >95% backbone perdeuteration achieved for chiral building blocks without loss of enantioselectivity.
  • Saccharomyces cerevisiae MBG5177 showed superior performance over baker's yeast for (2-2H1)solketal synthesis.
  • Pichia pastoris X-33 demonstrated >95% deuteration using methanol-d4.
  • MRR accurately measured site-specific deuteration and enantiopurity, simplifying process evaluation.

Conclusions:

  • Diverse microbial strains, not traditionally used in synthesis, are effective for isotope labeling.
  • Economical microbial deuteration methods are feasible using selected yeast strains and affordable deuterated sources.
  • Molecular rotational resonance spectroscopy is a valuable tool for analyzing deuterium-labeling processes.
  • This work advances isotope labeling and biocatalysis with implications for research and industry.