Water-soluble cavitands: synthesis of methylene-bridged resorcin[4]arènes containing hydroxyls and phosphates at their feet and bromomethyls and thiomethyls at their rims

Journal of Organic Chemistry

Volumn 63, Issue 20, 1998, Pages 6824-6829

  Mezo, Adam R ^a   Sherman, John C ^a  

^a UNIVERSITY OF BRITISH COLUMBIA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001497813     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980305k     Document Type: Article

References (34)

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4. For recent examples of unbridged resorcin[4]arenes, see: (a) Lewis, P. T.; Davis, C. J.; Saraiva, M. C.; Treleaven, W. D.; McCarley, T. D.; Strongin, R. M. J. Org. Chem. 1997, 62, 6110-6111.
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27. Cram, D. J.; Karbach, S.; Kim, Y. H.; Baczynshkyj, L.; Marti, K.; Sampson, R. M.; Kalleymeyn, G. W. J. Am. Chem. Soc. 1988,110, 2554-2560.
28. Perich, J. W.; Johns, R. B. Synth. Commun. 1988, 142-144. Attempts to purify DDP were unsuccessful.
29. The amino acid sequences of peptides 17 and 19 were designed such that each peptide would have a high propensity to form an amphiphilic a-helix and bundle with the other helices attached to the cavitand (ref 10). In addition, peptide 17 included a JV-terminal cysteine for reaction with benzyl bromide 11 while peptide 19 included a //terminal chloroacetyl group for reaction with benzylthiol 16. The structures and stabilities of de novo proteins 18 and 20 will be reported elsewhere. Standard one letter code abbreviations have been used for the amino acids: C = cysteine; E = glutamic acid; G = glycine; K = lysine; L = leucine.
30. The first water-soluble hemicarceplex was recently reported;40 however, its aqueous solubility was derived from its inter-bowl linkages. Such a method to attain water solubility greatly limits the variety of potential inter-bowl bridges and thus limits the cavity size. By attaining water solubility via the cavitand's pendent groups, carceplexes and hemicarceplexes are far more versatile candidates for supramolecular study and potential drug delivery systems.
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33. The 'H NMR signals from the tris-phosphate appeared as broad signals under those of the tetraphosphate.
34. Rink, H. Tetrahedron Lett. 1987, 28, 3787-3788.