Abstract
At the heart of host—guest chemistry is the design and construction of artificial receptors. While great progress has been achieved in the specific recognition of a multitude of substrates, rational design has still failed to equal the degree of association strength and substrate specificity observed in nature. Evolutionary selection has allowed biopolymers to take advantage of their large size to position varied functionality in the rigid context of tertiary structure, but the limitations of chemical synthesis dictate that artificial receptors will be smaller, less structurally defined, and, as a result, less effective. Combinatorial chemistry offers a new approach to the task of receptor design by quickly creating a library of combinatorial receptors containing a variety of binding or catalytic groups, and subsequently determining the most active component of that library (1–5}). Combinatorial receptors also provide the possibility for using substrate binding to selectively create a receptor from a dynamic library (6–8). To be effective, however, library synthesis should require minimal synthetic expenditure and the entire library must be screened efficiently.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
References
DeMiguel Y. R. and Sanders J. K. M. (1997) Generation and screening of synthetic receptor libraries. Curr. Op. Chem. Biol. 2, 417–421.
Chen C.-T., Wagner H., and Still W. C. (1998) Fluorescent, sequence-selective peptide detection by synthetic small molecules. Science 279, 851–853.
Haberhauer G., Somogyi L., and Rebek J. (2000) Synthesis of a second-generation pseudopeptide platform. Tetrahedron Lett. 41, 5013–5016.
Calama M. C., Hulst R., Fokkens R., Nibbering N. M. M., Timmerman P., and Reinhoudt D. N. (1998) Libraries of non-covalent hydrogen-bonded assemblies; combinatorial synthesis of supramolecular systems. Chem. Commun., 1021–1022.
Shimizu K. D., Snapper M. L., and Hoveyda A. H. (1998) High-throughput strategies for the discovery of catalysis. Chem. Eur. J. 4, 1885–1889.
Lehn J.-M. and Eliseev A. V. (2001) Dynamic combinatorial chemistry. Science 291, 2331–2332.
Epstein D. M., Choudhary S., Churchill M. R., Keil K. M., Eliseev A. V., and Morrow J. R. (2001) Chloroform-soluble schiff-base Zn(II) or Cd(II) complexes from a dynamic combinatorial library. Inorg. Chem. 40, 1591–1596.
Calama M. C., Timmerman P., and Reinhoudt D. N. (2000) Guest-templated selection and amplification of a receptor by noncovalent combinatorial synthesis. Angew. Chem. Int. Ed. 39, 755–757.
Linton B. and Hamilton A. (1997) Formation of artificial receptors by metaltemplated self-assembly. Chem. Rev. 97, 1669–1680.
Goodman M. S., Weiss J., and Hamilton A. D. (1994) A self-assembling receptor for dicarboxylic acids. Tetrahedron Lett. 35, 8943–8946.
Goodman M. S., Jubian V., and Hamilton A. D. (1995) Metal-templated receptors for the effective complexation of dicarboxylates. Tetrahedron Lett. 36, 2551–2554.
Goodman M. S., Hamilton A. D., and Weiss J. (1995) Self-assembling chromogenic receptors for the recognition of dicarboxylic acids. J. Am. Chem. Soc. 117, 8447–8455.
Constable E. C. and Thompson A. M. W. C. (1995) Strategies for the assembly of homo-and hetero-nuclear metalosupramolecules containing 2,2′:6′,2″-terpyridine metal-binding domains. J. Chem. Soc. Dalton Trans., 1615–1627.
Potts K. T., Usifer D. A., Guadalupe A., and Abruna H. D. (1987) 4-Vinyl, 6-vinyl, and 4'vinyl-2,2':6',2"terpyridinyl ligands: Their synthesis and the electrochemistry of their transition-metal coordination complexes. J. Am. Chem. Soc. 109, 3961–3967.
Goodman M. S., Jubian V., Linton B., and Hamilton A. D. (1995) A combinatorial library approach to artificial receptor design. J. Am. Chem. Soc. 117, 11610–11611.
Sauvage J.-P., Collin J.-P., Chambron J.-C., Guillerez S., and Coudret C. (1994) Ruthenium(II) and osmiun(II) bis(terpyridine) complexes in covalentlylinked multicomponent systems: Synthesis, electrochemical behavior, absorption spectra, and photochemical and photophysical properties. Chem. Rev. 94, 993–1019.
Constable E. C., Ward M. D., and Corr S. (1988) A convenient high yield synthesis of terpyridine. Inorg. Chim. Acta. 141, 201–203.
McCollum D. G., Yap G. P. A., Rhinegold A. L., and Bosnich B. (1996) Bimetallic reactivity—Synthesis of bimetallic complexes of macrocyclic binucleating ligands containing 6-coordinate and 4-coordinate sites and their reactivity with dioxygen and other oxidants. J. Am. Chem. Soc. 118, 1365–1379.
Linton B. and Hamilton A. D. (1999) Calorimetric investigation of guanidiniumcarboxylate interactions. Tetrahedron 55, 6027–6038.
Author information
Authors and Affiliations
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2002 Humana Press Inc.
About this protocol
Cite this protocol
Linton, B.R. (2002). Host—Guest Chemistry. In: English, L.B. (eds) Combinatorial Library. Methods in Molecular Biology™, vol 201. Springer, Totowa, NJ. https://doi.org/10.1385/1-59259-285-6:111
Download citation
DOI: https://doi.org/10.1385/1-59259-285-6:111
Publisher Name: Springer, Totowa, NJ
Print ISBN: 978-0-89603-980-3
Online ISBN: 978-1-59259-285-2
eBook Packages: Springer Protocols