A catenane whose stereochemistry is Euclidean but equivalent to that of reported topologically chiral catenanes
A catenane whose stereochemistry is Euclidean but equivalent to that of reported topologically chiral catenanes
In 1960, Wasserman synthesized a molecule in which two rings are held together like links in a chain. This molecule, which is called a catenane, is a topological isomer of the separated rings, which highlighted that molecules could be topologically non-trivial. This insight has found wider implications in biochemistry, where the topology of knotted and catenated proteins and oligonucleotides is thought to play a significant role in their properties, but it also led to the assumption that the stereochemistry of catenanes that are chiral due to the orientation of their rings is inherently topological in nature. Here we show that this assumption is incorrect by synthesizing an example that contains the same fundamental stereogenic unit but whose stereochemistry is Euclidean. Thus, we can unite the stereochemistry of catenanes with that of their topologically trivial cousins, the rotaxanes, paving the way for a more unified approach to their discussion.
Goldup, Stephen
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Rizzi, Federica
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Pairault, Noel G.M.
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Lozano, David
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Jamieson, Ellen M.G.
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Tizzard, Graham J.
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Goldup, Stephen
0a93eedd-98bb-42c1-a963-e2815665e937
Rizzi, Federica
aa3d273b-9877-42cf-8d80-9df6b8219788
Pairault, Noel G.M.
e0777b58-ccb8-41bf-84e4-7ab4ad203327
Lozano, David
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Jamieson, Ellen M.G.
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Tizzard, Graham J.
8474c0fa-40df-43a6-a662-7f3c4722dbf2
Goldup, Stephen, Rizzi, Federica, Pairault, Noel G.M., Lozano, David, Jamieson, Ellen M.G. and Tizzard, Graham J.
(2023)
A catenane whose stereochemistry is Euclidean but equivalent to that of reported topologically chiral catenanes.
Nature Chemistry.
(In Press)
Abstract
In 1960, Wasserman synthesized a molecule in which two rings are held together like links in a chain. This molecule, which is called a catenane, is a topological isomer of the separated rings, which highlighted that molecules could be topologically non-trivial. This insight has found wider implications in biochemistry, where the topology of knotted and catenated proteins and oligonucleotides is thought to play a significant role in their properties, but it also led to the assumption that the stereochemistry of catenanes that are chiral due to the orientation of their rings is inherently topological in nature. Here we show that this assumption is incorrect by synthesizing an example that contains the same fundamental stereogenic unit but whose stereochemistry is Euclidean. Thus, we can unite the stereochemistry of catenanes with that of their topologically trivial cousins, the rotaxanes, paving the way for a more unified approach to their discussion.
Text
rvsd1 MS NCHEM-22091835-T (figure 2 corrected)
- Accepted Manuscript
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Accepted/In Press date: 16 December 2023
Identifiers
Local EPrints ID: 474123
URI: http://eprints.soton.ac.uk/id/eprint/474123
ISSN: 1755-4330
PURE UUID: 87b4e225-ba2c-4fe1-9c92-f54eafca07f8
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Date deposited: 14 Feb 2023 17:31
Last modified: 31 Aug 2023 04:01
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Contributors
Author:
Federica Rizzi
Author:
David Lozano
Author:
Ellen M.G. Jamieson
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