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Developed by Professor Martin Burke and co-workers, the technology haspowerful implications for drug discovery, where the ability to quickly createlarge sets of related small molecules for use in screening is critical. Theadvancement relies on the use of a simple, low-cost, andenvironmentally-friendly ligand (N-methyliminodiacetic acid, "MIDA") thatreversibly modulates boronic acids toward cross-coupling. The MIDA-ligatedboronic acid building blocks can be used to construct target molecules using asingle cross-coupling reaction in an iterative process, in a fashionresembling peptide synthesis. Complex bioactive molecules can also beefficiently constructed, as demonstrated in recent publications from the Burkeresearch group in 2007 and 2008.
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"Sigma-Aldrich has a nearly 40-year history of developing boron reagentsfor use by the chemical community, and we are delighted to maintain ourleadership position in this area by garnering access to this potenttechnology," said Nate Wallock, Chemistry technology transfer manager atSigma-Aldrich. "In collaboration with the Burke group, our R&D groups haveactively developed the syntheses of dozens of MIDA boronic acid derivatives,many of which will be available globally in the coming weeks. We expect tooffer a broad set of these 'off-the-shelf' MIDA synthons, which will enablechemists to rapidly assemble complex chemical architectures using a singlepalladium-catalyzed reaction."
"This partnership brings together the strengths of a leader in thechemical industry with a first class research university ensuring that bothresearchers 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 tocontinuing to partner with Sigma-Aldrich on a wide range of new reagents."
In addition to applications in iterative cross-coupling, MIDA-protectedboronic acids (i.e., MIDA boronate esters) have substantially enhanced shelflives relative to the free boronic acids that often suffer from limited benchtop stability. Also, unlike other boronic acid derivatives that may exhibitreduced reactivity relative to their boronic acid counterparts, the MIDAboronate esters are cleaved under exceptionally mild conditions to release thecoupling-active boronic acid.
The MIDA technology highlights Sigma-Aldrich's continuing efforts toexpand its portfolio of proprietary catalysts, ligands, and organometallicbuilding blocks for use in cross-coupling. Detailed application informationon this technology and related products can be found athttp://sigma-aldrich.com/mida.
About Sigma-Aldrich: Sigma-Aldrich is a leading Life Science and HighTechnology company. Its biochemical and organic chemical products and kits areused in scientific and genomic research, biotechnology, pharmaceuticaldevelopment, the diagnosis of disease and as key components in pharmaceuticaland other high technology manufacturing. The Company has customers in lifescience companies, university and government institutions, hospitals, and inindustry. Over one million scientists and technologists use its products.Sigma-Aldrich operates in 36 countries and has 8,000 employees providingexcellent service worldwide. Sigma-Aldrich is committed to AcceleratingCustomer Success through Leadership in Life Science, High Technology andService. For more information about Sigma-Aldrich, please visit itsaward-winning website at http://www.sigma-aldrich.com.
Cautionary Statement: This release contains forward-looking statementsrelating to future performance, goals, strategic actions and initiatives andsimilar intentions and beliefs and other statements regarding the Companies'expectations, goals, beliefs, intentions and the like, which involveassumptions regarding the Companies' operations and conditions in the marketsthe Companies serve. The Companies do not undertake any obligation to updatethese forward-looking statements.
SOURCE Sigma-Aldrich
