Sigma-Aldrich is pleased to announce that it has signed an exclusive licensing agreement with the University of Illinois at Urbana-Champaign allowing Sigma-Aldrich to offer research quantities of powerful new boronic acid surrogates for use in Suzuki-Miyaura coupling to researchers worldwide. Under the terms of the agreement, Sigma-Aldrich can also satisfy commercial-scale requests for these surrogates from its manufacturing customers.
Developed by Professor Martin Burke and co-workers, the technology has powerful implications for drug discovery, where the ability to quickly create large sets of related small molecules for use in screening is critical. The advancement relies on the use of a simple, low-cost, and environmentally-friendly ligand (N-methyliminodiacetic acid, "MIDA") that reversibly modulates boronic acids toward cross-coupling. The MIDA-ligated boronic acid building blocks can be used to construct target molecules using a single cross-coupling reaction in an iterative process, in a fashion resembling peptide synthesis. Complex bioactive molecules can also be efficiently constructed, as demonstrated in recent publications from the Burke research group in 2007 and 2008.
"Sigma-Aldrich has a nearly 40-year history of developing boron reagents for use by the chemical community, and we are delighted to maintain our leadership position in this area by garnering access to this potent technology," said Nate Wallock, Chemistry technology transfer manager at Sigma-Aldrich. "In collaboration with the Burke group, our R&D groups have actively developed the syntheses of dozens of MIDA boronic acid derivatives, many of which will be available globally in the coming weeks. We expect to offer a broad set of these 'off-the-shelf' MIDA synthons, which will enable chemists to rapidly assemble complex chemical architectures using a single palladium-catalyzed reaction."
"This partnership brings together the strengths of a leader in the chemical industry with a first class research university ensuring that both researchers and commercial entities have access to these novel derivatives," stated Eric Payne, technology manager of the Office of Technology Management (OTM), of the University of Illinois at Urbana-Champaign. "We look forward to continuing to partner with Sigma-Aldrich on a wide range of new reagents."
In addition to applications in iterative cross-coupling, MIDA-protected boronic acids (i.e., MIDA boronate esters) have substantially enhanced shelf lives relative to the free boronic acids that often suffer from limited bench top stability. Also, unlike other boronic acid derivatives that may exhibit reduced reactivity relative to their boronic acid counterparts, the MIDA boronate esters are cleaved under exceptionally mild conditions to release the coupling-active boronic acid.
The MIDA technology highlights Sigma-Aldrich's continuing efforts to expand its portfolio of proprietary catalysts, ligands, and organometallic building blocks for use in cross-coupling. Detailed application information on this technology and related products can be found at http://sigma-aldrich.com/mida.