We are an organic chemistry research lab seeking to: (i) discover new catalysts and catalytic reactions; and (ii) use synthetic and supramolecular chemistry to develop new strategies to disrupt protein-protein interactions, which are implicated in many human diseases. Dr Peter Knipe
Lecturer in Organic Chemistry
Office: DKB 0G.109 I Tel: +44 (0)28 9097 4414 I @knipelab
Peter moved to Downing College, Cambridge in 2004 to study Natural Sciences, where he undertook a Master's project under the supervision of Professor Martin D. Smith investigating cascade approaches to bicyclic alkaloid natural products. In 2008, Peter moved to Oxford with Professor Smith to commence a DPhil, developing chiral counter-ion directed asymmetric electrocyclic reactions. His postdoctoral studies were also in Oxford, where he joined the lab of Professor Andrew D. Hamilton FRS. His work for Professor Hamilton included developing novel molecular switches, and the synthesis of α-helix and β-sheet secondary structural mimics as therapeutic agents to intercept protein-protein interactions. At the same time Peter was appointed as a Stipendiary Lecturer in Organic Chemistry in University College, Oxford.
In August 2016 Peter was appointed to the faculty at Queen's University, Belfast.
Catalysts for Enantioselective Synthesis
Selective, catalytic synthesis is vitally import to society, reducing the waste and energy requirements for the production of complex molecules and intermediates.
In general, asymmetric synthesis requires the formation of diastereomeric transition states that differ in energy sufficiently to give a bias towards a single enantiomeric product. One strategy to achieve this is by exploiting ion-pairing interactions between a charged, prochiral reaction intermediate and a homochiral catalyst ion bearing a complementary charge. The catalyst thus directs facial selectivity in the subsequent reaction, leading to enantioselectivity in the process overall. However, despite decades of research in this area, the range of available catalysts is limited. In the Knipe lab we are interested in developing new chiral scaffolds that will direct asymmetry in such processes, and in discovering new catalytic reactions that are amenable to this strategic approach.
Nature achieves its exquisite levels of selectivity and efficiency through a modular approach to synthesis: with just a few key building blocks (amino acids, nucleic acids and carbohydrates) it achieves a range of function that spans all of biology. In the context of proteins, this reactivity is made possible by the flexibility of these oligomers to adopt an almost infinite number of three-dimensional structures. In combination with evolutionary pressure and a timescale of aeons this leads to high levels of activity, despite the relatively limited 'alphabet' of catalytically-active proteinogenic amino acids.
Acid-Mediated Topological Control in a Functionalized Foldamer
Peter C. Knipe, S. Thompson and A. D. Hamilton, Chem. Comm. 2016, 52, 6521-6524. [link]
Hybrid Diphenylalkyne-Dipeptide Oligomers Induce Multi-Strand β-Sheet Formation
Jonathan E. Ross, Peter C. Knipe, Sam Thompson, Andrew D. Hamilton, Chem. Eur. J. 2015, 21, 13518-13521. [link]
A Modular Synthesis of Conformationally Preorganised Extended β-Strand Peptidomimetics
Tohru Yamashita, Peter C. Knipe, Nathalie Busschaert, Sam Thompson and Andrew D. Hamilton, Chem. Eur. J. 2015, 21, 14699-14702. [link]
Amphiphilic oligoamide α-helix peptidomimetics inhibit islet amyloid polypeptide aggregation
Oleg V. Kulikov, Sunil Kumar, Mazin Magzoub, Peter C. Knipe, Ishu Saraogi, Sam Thompson, Andrew D. Miranker and Andrew D. Hamilton. Tetrahedron Lett. 2015, 56, 3670-3673. [link]
b-Strand Mimetic Foldamers Ridgidified through Dipolar Repulsion
Elizabeth A. German, Jonathan E. Ross, Peter C. Knipe, Michaela F. Don, Sam Thompson and Andrew D. Hamilton. Angew. Chem. Int. Ed. 2015, 54, 2649-2652. [link]
Ion-Mediated Conformational Switches
Peter C. Knipe, Sam Thompson and Andrew D. Hamilton. Chem. Sci. 2015, 6, 1630-1639. [link]
Remote Conformational Control of a Molecular Switch via Methylation and Deprotonation
Peter C. Knipe, Ian M. Jones, Sam Thompson and Andrew D. Hamilton. Org. Biomol Chem. 2014, 12, 9384-9388. [link]
A Lewis acid-mediated conformational switch
Peter C. Knipe, Hannah Lingard, Ian M. Jones, Sam Thompson and Andrew D. Hamilton. Org. Biomol. Chem. 2014, 12, 7937-7941. [link]
Redox-Dependent Conformational Switching of Diphenylacetylenes
Ian M. Jones, Peter C. Knipe, Thoe Michaelos, Sam Thompson and Andrew D. Hamilton, Molecules 2014, 19, 11316-11332. [link]
Enantioselective one-pot synthesis of dihydroquinolones via BINOL-derived Lewis acid catalysis
Peter C. Knipe and Martin D. Smith, Org. Biomol. Chem. 2014, 12, 5094-5097. [link]
Phase-Transfer-Catalysed Synthesis of Pyrroloindolines and Pyridoindolines by a Hydrogen-Bond-Assisted Isocyanide Cyclization Cascade
Peter C. Knipe, Matija Gredicak, Artiom Cernijenko, Robert S. Paton and Martin D. Smith, Chem. Eur. J. 2014, 20, 3005-3009. [link]
Catalytic Enantioselective Electrocyclic Cascades
Eleanor E. Maciver, Peter C. Knipe, Andrew D. Cridland and Martin D. Smith, Chem. Sci. 2012, 3, 537-540. [link]
Asymmetric Electrocyclic Reactions
Sam Thompson, Anthony G. Coyne, Peter C. Knipe and Martin D. Smith. Chem. Soc. Rev. 2011, 40, 4217-4231. [link]
Molecular Recognition in Biomimetic Receptors in Macrocyclic and Supramolecular Chemistry: How Izatt-Christensen Award Winners Shaped the Field
Peter C. Knipe, Sam Thompson and Andrew D. Hamilton, ed. Reed M. Izatt, 2016, John Wiley and Sons, Ltd., Chichester, England. [link]
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