Charge-Tagged Proline-Based Organocatalyst for Mechanistic Studies Using ESI-MS
News Nov 14, 2014
A new 4-hydroxy-L-proline derivative with a charged 1-ethylpyridinium-4-phenoxy substituent has been synthesized with the aim of facilitating mechanistic studies of proline-catalyzed reactions by ESI mass spectrometry. The charged residue ensures a strongly enhanced ESI response compared to neutral unmodified proline. The connection by a rigid linker fixes the position of the charge tag far away from the catalytic center in order to avoid unwanted interactions. The use of a charged catalyst leads to significantly enhanced ESI signal abundances for every catalyst-derived species which are the ones of highest interest present in a reacting solution. The new charged proline catalyst has been tested in the direct asymmetric inverse aldol reaction between aldehydes and diethyl ketomalonate. Two intermediates in accordance with the List-Houk mechanism for enamine catalysis have been detected and characterized by gas-phase fragmentation. In addition, their temporal evolution has been followed using a microreactor continuous-flow technique.
The article, A new charge-tagged proline-based organocatalyst for mechanistic studies using electrospray mass spectrometry, is published in Beilstein Journal of Organic Chemistry and is free to access.
Penn Medicine Biochemist Receives Major Award for Research on Epigenetic Protein Modifications via Mass SpecNews
Benjamin A.Garcia, PhD, an expert in quantitative proteomics and Presidential Professor of Biochemistry and Biophysics in the Perelman School of Medicine at the University of Pennsylvania, has been awarded the Biemann Medal by the American Society for Mass Spectrometry (ASMS). The early-career award recognizes significant achievement in basic or applied mass spectrometry.
Exploring Challenges in the Synthesis of Pharmaceutical DrugsNews
This summer, Wendell and Loretta Hess Professor of Chemistry Ram Mohan will travel to India and Hong Kong to deliver a series of post-graduate workshops on advanced concepts in organic synthesis.
His workshop “Advanced Concepts in the Synthesis of Pharmaceutical Drugs” at the Indian Institute of Technology Indore will explore the unique, real-world challenges in the pharmaceutical industry to synthesize drugs that are both commercially viable and eco-friendly.
Modern Alchemists are Making Chemistry GreenerNews
Ancient alchemists tried to turn lead and other common metals into gold and platinum. Modern chemists in Paul Chirik’s lab at Princeton are transforming reactions that have depended on environmentally unfriendly precious metals, finding cheaper and greener alternatives to replace platinum, rhodium and other precious metals in drug production and other reactions.READ MORE
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