Advantages
- Low Cost and High Efficiency: This catalyst, combining boric acid with α-hydroxycarboxylic acid derivatives, is more cost-effective than conventional boronic acid catalysts.
- Environmentally Friendly: The reaction produces water as a sole byproduct, without waste generated from condensing agents.
- Highly Adaptable: By optimizing α-hydroxycarboxylic acid compounds, the catalyst can be tailored for use with a wide range of carboxylic acids and amines.
- High Yield: This catalyst is expected to enable high-yield production of pharmaceuticals and chemical products.
- Suppression of epimerization: Epimerization in peptide synthesis is minimized.
Technology Overview & Background
Amide bond formation through the dehydration-condensation reaction of carboxylic acids and amines, are crucial in the synthesis of various compounds, including peptides, low molecular weight compounds, and high molecular weight compounds such as nylon and aramid resins. These bonds are essential for the production of pharmaceuticals, agrochemical products, and other chemicals. Amide bond formation using condensing agents has been widely utilized for various compounds, including pharmaceuticals, owing to its high reliability. However, these reactions often produce byproducts from the condensing agents and pose challenges, such as epimerization in peptide synthesis. In contrast, catalyst-based reactions are considered ideal, as they generate water as the sole byproduct.
In 1996, Dr. Ishihara and his team at Nagoya University pioneered the use of boronic acid catalysts for amide bond formation. Since then, various types of boronic acid catalysts have been developed due to their environmental compatibility and high efficiency in amide synthesis. Additionally, inexpensive boric acid has also been explored as a catalyst; however, its application was previously limited by the requirement for high-temperature conditions.
In this study, researchers demonstrated that combining boric acid with α-hydroxycarboxylic acid facilitates the dehydration-condensation reaction of carboxylic acids and amines under mild conditions, successfully yielding amide compounds with high efficiency.
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Patent
- PCT/JP2024/008794 et al.
Principal Investigator & Academic Institution
Prof. Kazuaki ISHIHARA (Graduate School of Engineering, Nagoya University, Tokai National Higher Education and Research System)
Development Stages & Plans
- The catalyst demonstrated the high-yield dehydrative condensation of various carboxylic acids and amines. Amidation reactions at a 10 g scale have also demonstrated high yields.
- The catalyst demonstrated in the synthesis of dipeptides and tripeptides, achieving high yields while suppressing epimerization.
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- Improvements to further enhance catalyst activity are ongoing.
Collaboration Opportunities
TECH MANAGE CORP. are seeking:
- Companies interested in adopting this catalyst for amide synthesis.
- Condensing agent manufacturers interested in transitioning away from traditional condensing agent-based reactions.
Next Steps:
- A web meeting with Dr. Ishihara can be arranged to discuss the technology in detail.
- If you wish to conduct a feasibility study, such as synthesizing a specific amide compound of interest to your company, we are open to discussions on how to proceed in collaboration with our laboratory.
Please feel free to reach out for further discussions or to arrange a meeting.
Project No.TT-04573b