Noncovalent Chirality Sensing Ensembles for the Detection and Reaction Monitoring of Amino Acids, Peptides, Proteins, and Aromatic Drugs

Ternary complexes between the macrocyclic host cucurbit[8]uril, dicationic dyes, and chiral aromatic analytes afford strong induced circular dichroism (ICD) signals in the near‐UV and visible regions. This allows for chirality sensing and peptide‐sequence recognition in water at low micromolar analy...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2014-05, Vol.53 (22), p.5694-5699
Main Authors: Biedermann, Frank, Nau, Werner M.
Format: Article
Language:English
Subjects:
Amino Acid Sequence
Amino acids
Amino Acids - analysis
Animals
beta-Galactosidase - metabolism
Bridged-Ring Compounds - chemistry
Cattle
Chirality
Circular Dichroism
Circularity
cucurbiturils
Detection
Dichroism
Dyes
Enzyme Assays
Enzymes
Fluorescent Dyes - chemistry
Imidazoles - chemistry
Leucyl Aminopeptidase - metabolism
macrocycles
Molecular Sequence Data
Monitoring
Peptides
Peptides - analysis
Pharmaceutical Preparations - analysis
Proteins - analysis
sequence recognition
Serum Albumin, Bovine - analysis
Stereoisomerism
supramolecular chemistry
Water - chemistry
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Summary:Ternary complexes between the macrocyclic host cucurbit[8]uril, dicationic dyes, and chiral aromatic analytes afford strong induced circular dichroism (ICD) signals in the near‐UV and visible regions. This allows for chirality sensing and peptide‐sequence recognition in water at low micromolar analyte concentrations. The reversible and noncovalent mode of binding ensures an immediate response to concentration changes, which allows the real‐time monitoring of chemical reactions. The introduced supramolecular method is likely to find applications in bioanalytical chemistry, especially enzyme assays, for drug‐related analytical applications, and for continuous monitoring of enantioselective reactions, particularly asymmetric catalysis. Strong and diagnostic induced circular dichroism signals in the near‐UV or visible region are obtained when chiral, optically transparent analytes bind to an achiral chemosensing ensemble composed of a macrocyclic host and dye. This affords a novel, supramolecular detection method for chiral aromatic analytes in water.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201400718