Tuning of Binding Selectivity:  Metal Control of Organic Guest Binding and Allosteric Perturbation of Fluorescent Metal Sensor

Ligand 1, bearing two ethylenediamine groups, was designed to form a hydrophobic cavity upon binding to metals. The shape of its nonpolar cavity depends on the metal:  a reversal in binding preference for naphthalene or biphenyl groups is found when the metal is changed from zinc to copper, with a s...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 64; no. 24; pp. 8922 - 8928
Main Authors Wang, Fen, Schwabacher, Alan W
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 26.11.1999
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
CU(II) ION
PHOSPHINATE
DESIGN
LIQUID-CHROMATOGRAPHY
CHEMOSENSORS
RECOGNITION
AMINO-ACIDS
CHEMISTRY
DENDRIMERS
WATER
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Summary:Ligand 1, bearing two ethylenediamine groups, was designed to form a hydrophobic cavity upon binding to metals. The shape of its nonpolar cavity depends on the metal:  a reversal in binding preference for naphthalene or biphenyl groups is found when the metal is changed from zinc to copper, with a selectivity change of 260-fold. In the presence of dansylated amino acids, the new ligand constitutes a fluorescent sensor for zinc ion. Variations are seen in affinity for dansylamino acid with minor structural changes, and organic selectivity changes with complexes of variant metals. These findings suggest that sensor tuning of affinity and selectivity for metal is possible by choice of simple organic guest and for organic guest by choice of metal.
Bibliography:ark:/67375/TPS-F6451JDV-5
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ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/jo991246t