Abstract
THE construction of synthetic molecules that fold or assemble predictably into large, well defined structures represents a fertile area of chemistry. Many supramolecular systems have been reported that self-assemble as a result of non-covalent interactions1-7; and the control of higher-order protein structure by de novo design has also been demonstrated8,9. Protein secondary structural motifs have also been stabilized by incorporating artificial groups that impose constraints on the folded architecture10-12. Here we describe the synthesis of molecules that will fold in water into a pleated structure, as a result of interactions between alternating electron-rich donor groups and electron-deficient acceptor groups. We verify the pleated structure using absorption and NMR spec-troscopy. Donor-acceptor interactions have been used previously to engineer specific supramolecular geometries2,13, and are energetically favourable in organic as well as in aqueous solutions. But whereas previously such interactions have been used to effect self-assembly of distinct molecules, our results show that they can also determine the secondary structure of complex synthetic molecules in solution.
This is a preview of subscription content
Access options
Subscribe to Journal
Get full journal access for 1 year
$199.00
only $3.90 per issue
All prices are NET prices.
VAT will be added later in the checkout.
Tax calculation will be finalised during checkout.
Buy article
Get time limited or full article access on ReadCube.
$32.00
All prices are NET prices.
References
Lindsey, J. S. New J. Chem. 15, 153–180 (1991).
Amabilino, D. B. et al. J. Am. chem. Soc. 117, 1271–1294 (1995).
Whitesides, G. M., Mathias, J. P. & Seto, C. T. Science 254, 1312–1319 (1991).
Lehn, J.-M. Angew. Chem. int. Edn engl. 29, 1304–1319 (1990).
Chambron, J. C., Dietrich-Buchecker, C. O., Heitz, V., Nierengarten, J.-F. & Sauvage, J.-P. in Transition Metals in Supramolecular Chemistry (eds Fabbrizzi, L. & Poggi, A.) 371–390 (Kluwer Academic, Dordrecht, 1994).
Ashton, P. R., Philp, D., Spencer, J. & Stoddart, J. F. J. chem. Soc., chem. Commun. 1677–1679 (1991).
LaBrenz, S. R. & Kelly, J. W. J. Am. chem. Soc. 117, 1655–1656 (1995).
Betz, S. F., Raleigh, D. P. & Degrado, W. F. Curr. Opin. struct. Biol. 3, 601–610 (1993).
Quinn, T. P., Tweedy, N. B., Richardson, J. S., Williams, R. W. & Richardson, D. C. Proc. natn. Acad. Sci. U.S.A. 91, 8747–8751 (1994).
Mutter, M. et al. J. Am. chem. Soc. 114, 1463–1470 (1992).
Ghadiri, M. R., Soares, C. & Choi, C. J. Am. chem. Soc. 114, 825–831 (1992).
Åkerfeldt, K. S., Kim, R. M., Comac, D., Groves, J. T., Lear, J. D. & DeGrado, W. F. J. Am. chem. Soc. 114, 9656–9657 (1992).
Hunter, C. A. & Sanders, J. R. M. J. Am. chem. Soc. 112, 5525–5534 (1990).
Hanna, M. W. & Ashbaugh, A. L. J. phys. Chem. 68, 811–816 (1964).
Deranleau, D. A. J. Am. chem. Soc. 91, 4044–4054 (1969).
Benniston, A. C., Harriman, A. & Lynch, V. M. Tetrahedron Lett. 35, 1473–1476 (1994).
Cantor, R. C. & Schimmel, P. R. Biophysical Chemistry Part II 390–408 (Freeman, New York, 1980).
Chudek, J. A., Foster, R. & Twiselton, D. R. J. chem. Soc. Perkin Trans. II 1385–1389 (1983).
Barlos, K. et al. Tetrahedron Lett. 30, 3943–3946 (1989).
Atherton, E. & Shepard, R. C. Solid Phase Peptide Synthesis (IRL, Oxford, 1989).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Scott Lokey, R., Iverson, B. Synthetic molecules that fold into a pleated secondary structure in solution. Nature 375, 303–305 (1995). https://doi.org/10.1038/375303a0
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1038/375303a0
Further reading
-
Designing cooperatively folded abiotic uni- and multimolecular helix bundles
Nature Chemistry (2018)
-
Photomodulation of fluoride ion binding through anion-π interactions using a photoswitchable azobenzene system
Scientific Reports (2016)
-
Halogen Bonding in the Assembly of Silver(I)-ethynide Complexes with 1-Iodo-3,5-bis(prop-2-ynyloxy)benzene
Journal of Cluster Science (2016)
-
Iterative design of a helically folded aromatic oligoamide sequence for the selective encapsulation of fructose
Nature Chemistry (2015)
-
Spectroscopic studies on the photostability and photoactivity of metallo-tetraphenylporphyrin in micelles
Colloid and Polymer Science (2014)
Comments
By submitting a comment you agree to abide by our Terms and Community Guidelines. If you find something abusive or that does not comply with our terms or guidelines please flag it as inappropriate.