Abstract
The vancomycin family of antibiotics offers an attractive target in synthetic host-guest chemistry. Vancomycin (1) has been shown by 1H nmr toform discreet complexes with the -D-Ala-D-Ala fragment found in bacterial cell walls. The structure of the active complex (2) involves six hydrogen bonds between the antibiotic and dipeptide substrate. The complexation is strongly substrate- and stereoselective due to the concave nature of the cavity formed by the biphenyl and triphenyl diether components. Our interest lies in designing synthetic analogs of vancomycin both as novel receptors for peptide carboxylate substrates and as potentially interesting antibiotics.
This is a preview of subscription content, log in via an institution to check access.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
References
M.P. Williamson and D. H. Williams, J. Am. Chem. Soc. 1981, 103, 6580. M. P. Williamson, D. H. Williams, and S. J. Hammond, Tetrahedron, 1984, 40, 569.
Author information
Authors and Affiliations
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 1987 D. Reidel Publishing Company
About this paper
Cite this paper
Pant, N., Mann, M., Hamilton, A.D. (1987). Synthetic Analogs of Peptide-Binding Antibiotics. In: Atwood, J.L., Davies, J.E.D. (eds) Inclusion Phenomena in Inorganic, Organic, and Organometallic Hosts. Advances in Inclusion Science, vol 4. Springer, Dordrecht. https://doi.org/10.1007/978-94-009-3987-5_15
Download citation
DOI: https://doi.org/10.1007/978-94-009-3987-5_15
Publisher Name: Springer, Dordrecht
Print ISBN: 978-94-010-8269-3
Online ISBN: 978-94-009-3987-5
eBook Packages: Springer Book Archive