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
--- up 3 weeks, 3 days, 10 hours, 51 minutes
* Origin: -=> Castle Rock BBS <=- Now Husky HPT Powered! (1:317/3)