• Cheap, eco-friendly catalyst opens new p

    From ScienceDaily@1:317/3 to All on Thursday, March 24, 2022 22:30:44
    Cheap, eco-friendly catalyst opens new possibilities for organic
    molecules built from pyruvate

    Date:
    March 24, 2022
    Source:
    Okinawa Institute of Science and Technology (OIST) Graduate
    University
    Summary:
    Chemists have developed an organic catalyst that can drive reactions
    using pyruvate -- a key biomolecule in many metabolic pathways --
    that are difficult and complicated to achieve using conventional
    industrial techniques. The research is an important step towards
    simplifying the production process and increasing the range of
    molecules that can be built from pyruvate, like amino acids or
    glycolic acids, which are used in drug discovery efforts and
    medications.



    FULL STORY ========================================================================== Chemists at the Okinawa Institute of Science and Technology Graduate
    University (OIST) have developed an organic catalyst that can drive
    reactions using pyruvate -- a key biomolecule in many metabolic pathways
    -- that are difficult and complicated to achieve using conventional
    industrial techniques.


    ==========================================================================
    The research, recently published in Organic Letters, is an important step towards simplifying the production process and increasing the range of molecules that can be built from pyruvate, like amino acids or glycolic
    acids, which are used in drug discovery efforts and medications.

    "Catalysts, substances which control and accelerate chemical reactions
    without being included into the final products, are crucial tools for chemists," said Santanu Mondal, a PhD candidate in Chemistry and Chemical Bioengineering Unit at OIST and first author of the study. "And organic catalysts, in particular, are set to revolutionize the industry and
    make chemistry more sustainable." Currently, metal catalysts are used
    in industry, which are often expensive to obtain and produce hazardous
    waste. Metal catalysts also react easily with air and water, making
    them difficult to store and handle. But organic catalysts are formed
    from common elements, like carbon, hydrogen, oxygen, and nitrogen,
    so they are much cheaper, safer and more environmentally friendly.

    "On top of these advantages, our newly developed organic catalyst system
    also promotes reactions using pyruvate that aren't easily achievable
    using metal catalysts," added Santanu.

    In all chemical reactions, he went on to explain, molecules can react by
    either giving away electrons, or receiving them. Pyruvate is much better
    at receiving electrons when it reacts and is typically used this way in industry, to produce organic alcohols and solvents. But within our bodies, protein catalysts called enzymes can drive reactions in which pyruvate
    donates electrons to produce molecules like fatty acids and amino acids.



    ==========================================================================
    By taking inspiration from these enzymes, the researchers designed
    a catalyst system made of two small organic molecules, an acid and an
    amine, that forces pyruvate to act as an electron donor.

    In the reaction, the amine binds to pyruvate, making an intermediate
    molecule.

    The acid then covers up part of the intermediate molecule, while leaving another part, which can donate electrons, free to react and form a
    new product.

    Importantly, the catalyst system is highly selective about which form
    of the product it will make. Like our hands, many biomolecules are
    asymmetric and can exist in two forms that are mirror-images of each
    other. These molecules look similar, but often have differing properties.

    "Organic catalysts can be designed in a way that at the end of
    the reaction, only one of these mirror-image forms is made," said
    Santanu. "This is particularly beneficial in the pharmaceutical industry,
    where one of the forms may be an effective treatment, but the other form
    may be toxic." For the pyruvate reactions, the researchers were able
    to selectively choose which of the two mirror-image forms of the final
    product to make, by changing which mirror-image form of the amine was
    used to catalyze the reaction.

    Currently, the organic catalyst system only works when reacting pyruvate
    with a specific class of organic molecule, called cyclic imines. But ultimately, the research team dream of creating a next-generation catalyst
    for pyruvate that is universal, meaning that it can speed up reactions
    between pyruvate and a broad range of organic molecules.

    "With a universal catalyst, chemists would be able to easily make an
    array of various products from pyruvate, in both mirror-image forms,"
    said Santanu.

    "This would have many meaningful impacts on society, such as speeding
    up the development of new drugs."

    ========================================================================== Story Source: Materials provided by Okinawa_Institute_of_Science_and_Technology_(OIST)
    Graduate_University. Original written by Dani Ellenby. Note: Content
    may be edited for style and length.


    ========================================================================== Journal Reference:
    1. Santanu Mondal, Ravindra D. Aher, Venkati Bethi, Yu-Ju Lin, Tohru
    Taniguchi, Kenji Monde, Fujie Tanaka. Control of Reactions of
    Pyruvates by Catalysts: Direct Enantioselective Mannich Reactions
    of Pyruvates Catalyzed by Amine-based Catalyst Systems. Organic
    Letters, 2022; 24 (9): 1853 DOI: 10.1021/acs.orglett.2c00436 ==========================================================================

    Link to news story: https://www.sciencedaily.com/releases/2022/03/220324143812.htm

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