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Bhattarai KM, Davis AP, Perry JJ, et al. A New Generation of "Cholaphanes": Steroid-Derived Macrocyclic Hosts with Enhanced Solubility and Controlled Flexibility. J Org Chem. 1997;62(24):8463-8473doi: 10.1021/jo971272w.
Bhattarai, K. M., Davis, A. P., Perry, J. J., Walter, C. J., Menzer, S., & Williams, D. J. (1997). A New Generation of "Cholaphanes": Steroid-Derived Macrocyclic Hosts with Enhanced Solubility and Controlled Flexibility. The Journal of organic chemistry, 62(24), 8463-8473. https://doi.org/10.1021/jo971272w
Bhattarai, Khadga M., et al. "A New Generation of "Cholaphanes": Steroid-Derived Macrocyclic Hosts with Enhanced Solubility and Controlled Flexibility." The Journal of organic chemistry vol. 62,24 (1997): 8463-8473. doi: https://doi.org/10.1021/jo971272w
Bhattarai KM, Davis AP, Perry JJ, Walter CJ, Menzer S, Williams DJ. A New Generation of "Cholaphanes": Steroid-Derived Macrocyclic Hosts with Enhanced Solubility and Controlled Flexibility. J Org Chem. 1997 Nov 28;62(24):8463-8473. doi: 10.1021/jo971272w. PMID: 11671987.
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J Org Chem. 1997 Nov 28;62(24):8463-8473. doi: 10.1021/jo971272w.

A New Generation of "Cholaphanes": Steroid-Derived Macrocyclic Hosts with Enhanced Solubility and Controlled Flexibility.

The Journal of organic chemistry

Khadga M. Bhattarai, Anthony P. Davis, Justin J. Perry, Christopher J. Walter, Stephan Menzer, David J. Williams

Affiliations

  1. Department of Chemistry, Imperial College of Science and Technology, South Kensington, London SW7 2AY, U.K.

PMID: 11671987 DOI: 10.1021/jo971272w

Abstract

The macrocyclic "cholaphanes" 3a-c were synthesized from the inexpensive steroid cholic acid. Like earlier relatives they feature substantial cavities with inward-directed hydroxyl groups, suitable for binding polar molecules such as carbohydrates in nonpolar media. New features are the externally directed alkyl chains, promoting solubility in organic solvents, and (in the case of 3b/c) reduced conformational freedom resulting from truncation of the steroidal side-chain. In particular, modeling shows that the smallest macrocycle 3c possesses very little flexibility, preferring an open conformation which is also revealed in the X-ray crystal structure of its pentahydrate. NMR studies indicated that all three cholaphanes form 1:1 complexes with octyl beta-D-glucoside in CDCl(3), with K(a) = 600-1560 M(-)(1). Cholaphanes 3b/c proved able to extract methyl beta-D-glucoside from aqueous solutions into CHCl(3). The transport of methyl beta-D-glucoside across a chloroform barrier was also demonstrated for 3c.

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