Events Calendar
Mar 27
14:00 - 15:00
G. Dan Pantoș Department of Chemistry, University of Bath:Chirality in Dynamic Combinatorial Chemistry
Physical Sciences colloquia

Chirality is at the core of all biological processes as it influences protein (mis)folding, substrate recognition etc. Unsurprisingly, point chirality impacts the outcome of dynamic combinatorial libraries (DCLs). In some cases, enantiomeric or diastereomeric products are formed when chiral building blocks are combined, while in other cases structural divergence is observed. Structurally Divergent Reactions on Racemic Mixtures (SDRRM) lead to two distinct chemical entities starting from two enantiomers[1]. 

We will discuss the outcomes of chiral DCLs including the first Dynamic Combinatorial approach to generate structural divergence from racemic building blocks. The divergence is due to a combination of a kinetic resolution during the synthesis of diastereomeric macrocycles and a stereospecific electron-donor (D) – electron-acceptor (A) interaction, leading to structurally distinct pseudorotaxanes. 

These factors, combined with a difference in the stability of the final products, lead to the spontaneous assembly of two structurally different, non-isomeric [2]catenanes: one with a DAAD aromatic stack, while the other has a DADD stack. This work provides a new approach towards understanding and developing SDRRMs and raises the possibility of supramolecular interactions in aqueous media, playing a crucial role in the biological world's homochirality[2,3]. References:1. Miller, L. C. & Sarpong, R. Chem. Soc. Rev. 2011, 40, 4550-4562.2. Guijarro, A. & Yus, M. The Origin of Chirality in the Molecules of Life: a Revision from Awareness to the Current Theories and Perspectives of this Unsolved Problem.(Royal Society of Chemistry, Cambridge, UK, 2008).3. Amplification of Chirality (Ed. K. Soai). Topics in Current Chemistry 2008, 284, 1-201.

Location

Ingram Lecture Theatre
United Kingdom

Details

Open to all,

Contact: Helena Shepherd
E: H.J.Shepherd@kent.ac.uk
School of Physical Sciences

 

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