Size discrimination in intramolecular complexation of modified a-cyclodextrins: a preparative and nuclear magnetic resonance study
Date
2001
Authors
Lock, J.
May, B.
Clements, P.
Tsanaktsidis, J.
Easton, C.
Lincoln, S.
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Advisors
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Journal article
Citation
Organic and Biomolecular Chemistry, 2001; 1(24):3361-3364
Statement of Responsibility
Julia S. Lock, Bruce L. May, Philip Clements, John Tsanaktsidis, Christopher J. Easton and Stephen F. Lincoln
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DOI
Abstract
Acylation of the primary amine group of 6<sup>A</sup>-(6-aminohexylamino)-6<sup>A</sup>-deoxy-α-cyclodextrin 1 by 4-nitrophenyl trinorbornane-2-acetate 6, 1-methoxycarbonyl-8-(4-nitrophenoxycarbonyl)cubane 7, 1-methoxycarbonyl-2,3-dimethyl-8-(4-nitrophenoxycarbonyl)cubane 8, and 1-(4-nitrophenoxycarbonyl)adamantane 9, respectively, gives 6<sup>A</sup>-deoxy-[6-(trinorbornan-2-ylacetylamino)hexylamino]-α- cyclodextrin 2, 6<sup>A</sup>-[6-(8-carboxycuban-1-ylcarbonyl-amino)hexylamino]-6 <sup>A</sup>-deoxy-α-cyclodextrin 3, 6<sup>A</sup>-[6-(8-carboxy-2,3-dimethylcuban-l-ylcarbonylamino)hexylamino]- 6<sup>A</sup>-deoxy-α-cyclodextrin 4, and 6<sup>A</sup>-[6-(adamantan-1-ylcarbonylamino)hexylamino]-6<sup>A</sup>- deoxy-α-cyclodextrin 5, in good yields together with 4-nitrophenolate. In basic D<sup>2</sup>O, the substituents of 1-4 complex intramolecularly within the α-cyclodextrin annulus, whereas that of 5 does not due to its larger size, as shown by <sup>1</sup>H ROESY NMR spectroscopy. This facilitates a mechanistic comparison with the formation of βCD analogues of 2-5.
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© Royal Society of Chemistry 2001