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Sigma-Aldrich to Develop New Boronic Acid Surrogates for Chemistry Community

University of Illinois at Urbana-Champaign and Sigma-Aldrich® have entered into a licensing agreement which enables Sigma-Aldrich to expand the range of a powerful class of boronic acid surrogates offered to the global chemistry community.

Boronic acids are building blocks for Suzuki-Miyaura cross-couplings, one of the most widely used chemical reactions to form carbon-carbon bonds. Sigma-Aldrich plans to utilize an innovative technology developed by Professor Martin Burke of the University of Illinois at Urbana-Champaign to produce surrogates for boronic acids previously not easily accessible. The availability of these surrogates is expected to greatly enhance the syntheses of many chemically important small molecules such as pharmaceuticals and natural products.

“We believe the simple, IP-inclusive model provides our customers freedom to incorporate the materials into the broadest range of synthetic routes.”
.Through a license to Professor Burke’s earlier developed technology, Sigma-Aldrich currently offers MIDA boronates to researchers and manufacturing customers. In MIDA boronates, a ligand (N-methyliminodiacetic acid, "MIDA") protects the acid functionality of boronic acids rendering the boronates stable towards unwanted reactions and decomposition. The ligand can easily be removed in a controlled fashion under mild aqueous basic conditions, liberating the acid for coupling reactions. The new work from Professor Burke’s laboratory provides routes to MIDA boronates where the analogous acids are highly desired but unstable and often difficult to synthesize.

MIDA boronates can also be used in iterative cross-coupling reactions where small molecules can be synthesized in a modular manner similar to fabrication of biosynthetic systems such as polypeptides, oligonucleotides, and oligosaccharides.

Sigma-Aldrich will offer a label license where purchasers have a royalty-free license to the University of Illinois’ intellectual property in use of the MIDA boronates. Through this arrangement, the University hopes to encourage adoption of the technology throughout many industries.

“Sigma-Aldrich currently offers more than seventy MIDA boronates to the global chemistry community. We aim to actively expand this portfolio, making available highly enabling building blocks such as 2-heterocyclic boronate derivatives,” said Nate Wallock, Chemistry Technology Transfer Manager at Sigma-Aldrich. “We believe the simple, IP-inclusive model provides our customers freedom to incorporate the materials into the broadest range of synthetic routes.”

“We believe this unique label license will catalyze wide use of the MIDA boronate platform, “ said Lesley Millar, Director of the Office of Technology Management at the University of Illinois at Urbana-Champaign. “By removing ambiguity about how intellectual property may be handled down-stream, companies are encouraged to incorporate the technology into all phases of its development and manufacturing.”

Professor Burke is in the Department of Chemistry at the University of Illinois at Urbana-Champaign and is an Early Career Scientist of the Howard Hughes Medical Institute.

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