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Development of a Packed Bed Reactor for the Synthesis of Peptides and Foldamers: A Revolutionary Reduction of the Amino Acid Excess

Video   Jul 31, 2015

 



About the Speaker
István M. Mándity was born in Baja, Hungary, in 1983. After obtaining his MSc in Pharmacy from University of Szeged, Hungary, in 2006, he earned his PhD degree at the same university in 2011. He is head of the Structural Analysis Laboratory of the Institute of Pharmaceutical Chemistry (Szeged). His research focuses on flow chemistry and foldamers. His cumulative impact factor is 125.869 and the number of independent citations is 351.Abstract
The importance of synthesis of peptides warranted by the need for peptide-based medicines, the roles of peptides and foldamers in drug discovery, etc. Since its introduction by Merrifield, peptide synthesis was performed almost exclusively on solid supports. It has been applied for the synthesis of foldamers as well. However, still a general property of these methodologies are the high number of amino acid equivalents required for total coupling. Continuous-flow (CF) approaches have recently gained in significance among synthetic techniques. We show here that the number of amino acid equivalents used for SPPS can be lowered drastically to around 1.5 equivalents through the application of a CF technique and by complete reaction parameter optimization. Under the optimized conditions the couplings of all 20 proteinogenic amino acids with 1.5 amino acid equivalents proceeded with excellent conversions. To demonstrate the efficiency of the CF-SPPS methodology, known difficult sequences were synthetized in automated way. As further evidence of the effectiveness, ß-peptide foldamers with alicyclic side-chains were synthetized in excellent yields. Importantly, exotic and expensive artificial amino acids were incorporated into sequences by an automated way through the use of exceptionally low numbers of amino acid equivalents at low costs.

 
 
 
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