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https://hdl.handle.net/2440/4817
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Type: | Journal article |
Title: | Square pegs in round holes. Preparation and intramolecular complexation of cubyl substituted b-cyclodextrins and of an adamantane analogue |
Author: | May, B. Clements, P. Tsanaktsidis, J. Easton, C. Lincoln, S. |
Citation: | Organic and Biomolecular Chemistry, 2000; 3(3):463-469 |
Publisher: | Royal Society of Chemistry |
Issue Date: | 2000 |
ISSN: | 1472-7781 1470-4358 |
Statement of Responsibility: | Bruce L. May, Philip Clements, John Tsanaktsidis, Christopher J. Easton and Stephen F. Lincoln |
Abstract: | The reaction of either 1-methoxycarbonyl-4-(4-nitrophenoxycarbonyl)cubane or its dimethyl analogue, 2,3-dimethyl-1-methoxycarbonyl-4-(4-nitrophenoxycarbonyl)cubane, with the primary amine of 6A-(6-aminohexyl) amino-6A-deoxy-β-cyclodextrin produces the first cubyl substituted β-cyclodextrins, 6A-deoxy-6A- {6-[N-(4-methoxycarbonylcuban-1-ylcarbonyl)amino]hexylamino}-β-cyclodextrin and its dimethyl analogue, respectively, and 4-nitrophenolate. The reaction of 1,4-bis(4-nitrophenoxycarbonyl)cubane with 6A-(6-aminohexyl) amino-6A-deoxy-β-cyclodextrin produces the dimer 1,4-bis{6-[N-(6A-deoxy-β-cyclodextrin-6A-yl)amino]- hexylaminocarbonyl}cubane. 1H NMR ROESY studies are consistent with the cubyl moiety of each of the above three cubyl-substituted β-cyclodextrins complexing in the β-cyclodextrin annuli in D2O. The reaction of 1-(4-nitrophenoxycarbonyl)adamantane with β-cyclodextrin produces 6A-{6-[N-(1-adamantylcarbonyl)amino]- hexylamino}-6A-deoxy-β-cyclodextrin which shows a strong intramolecular complexation of its adamantyl moiety. Adamantane-1-carboxylate forms intermolecular complexes with the above three cubyl-substituted β-cyclodextrins in D2O solution and excludes the cubyl moiety from the β-cyclodextrin annulus. However, this does not occur for 6A-{6-[N-(1-adamantylcarbonyl)amino]hexylamino}-6A-deoxy-β-cyclodextrin where intramolecular complexation appears to be sufficiently strong to prevent intermolecular complexation of adamantane-1-carboxylate. |
Description: | Copyright © 2000 The Royal Society of Chemistry |
DOI: | 10.1039/a905390e |
Published version: | http://dx.doi.org/10.1039/a905390e |
Appears in Collections: | Aurora harvest 2 Chemistry publications Environment Institute publications |
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