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.
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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.
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© 1987 D. Reidel Publishing Company
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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
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DOI: https://doi.org/10.1007/978-94-009-3987-5_15
Publisher Name: Springer, Dordrecht
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