Please use this identifier to cite or link to this item:
https://hdl.handle.net/2440/4817
Citations | ||
Scopus | Web of Science® | Altmetric |
---|---|---|
?
|
?
|
Full metadata record
DC Field | Value | Language |
---|---|---|
dc.contributor.author | May, B. | - |
dc.contributor.author | Clements, P. | - |
dc.contributor.author | Tsanaktsidis, J. | - |
dc.contributor.author | Easton, C. | - |
dc.contributor.author | Lincoln, S. | - |
dc.date.issued | 2000 | - |
dc.identifier.citation | Organic and Biomolecular Chemistry, 2000; 3(3):463-469 | - |
dc.identifier.issn | 1472-7781 | - |
dc.identifier.issn | 1470-4358 | - |
dc.identifier.uri | http://hdl.handle.net/2440/4817 | - |
dc.description | Copyright © 2000 The Royal Society of Chemistry | - |
dc.description.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. | - |
dc.description.statementofresponsibility | Bruce L. May, Philip Clements, John Tsanaktsidis, Christopher J. Easton and Stephen F. Lincoln | - |
dc.language.iso | en | - |
dc.publisher | Royal Society of Chemistry | - |
dc.source.uri | http://dx.doi.org/10.1039/a905390e | - |
dc.title | Square pegs in round holes. Preparation and intramolecular complexation of cubyl substituted b-cyclodextrins and of an adamantane analogue | - |
dc.type | Journal article | - |
dc.identifier.doi | 10.1039/a905390e | - |
pubs.publication-status | Published | - |
Appears in Collections: | Aurora harvest 2 Chemistry publications Environment Institute publications |
Files in This Item:
There are no files associated with this item.
Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.