Mono-acylation of a polyamine-β-cyclodextrin based on guest mediated acyl migration

The S → N acylation rates of thioester functionalized coumarins on heptakis-[6-deoxy-6-(2-aminoethylsulfanyl)]-β-cyclodextrin were measured. A high yield of mono-acylation was achieved with products that form self-inclusion compounds. The differential fluorescence response of the functionalized cycl...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2011-08, Vol.47 (30), p.8614-8616
Main Authors: Gómez-Biagi, Rodolfo F, Nitz, Mark
Format: Article
Language:English
Subjects:
Acylation
Coumarins - chemistry
Cyclodextrins - chemistry
Polyamines - chemistry
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Summary:The S → N acylation rates of thioester functionalized coumarins on heptakis-[6-deoxy-6-(2-aminoethylsulfanyl)]-β-cyclodextrin were measured. A high yield of mono-acylation was achieved with products that form self-inclusion compounds. The differential fluorescence response of the functionalized cyclodextrins upon binding biomacromolecules shows the potential of the constructs as probes.
ISSN:1359-7345
1364-548X
DOI:10.1039/c1cc12646f