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 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.
School of Engineering and Science, Jacobs University Bremen, Campus Ring 1, 28759 Bremen (Germany). frankbiedermann@daad-alumni.de.
Frank
F
Biedermann
Werner M
WM
Nau
D000595:Amino Acid Sequence; D000596:Amino Acids / Q000032:analysis*; D000818:Animals; D001952:Bridged-Ring Compounds / Q000737:chemistry; D002417:Cattle; D002942:Circular Dichroism; D057075:Enzyme Assays; D005456:Fluorescent Dyes / Q000737:chemistry; D007093:Imidazoles / Q000737:chemistry; D007931:Leucyl Aminopeptidase / Q000378:metabolism; D008969:Molecular Sequence Data; D010455:Peptides / Q000032:analysis*; D004364:Pharmaceutical Preparations / Q000032:analysis*; D011506:Proteins / Q000032:analysis*; D012710:Serum Albumin, Bovine / Q000032:analysis; D013237:Stereoisomerism; D014867:Water / Q000737:chemistry; D001616:beta-Galactosidase / Q000378:metabolism; D047028:Macrocyclic Compounds; D000099246:Cucurbit(n)urils
D000596:Amino Acids; D001952:Bridged-Ring Compounds; D005456:Fluorescent Dyes; D007093:Imidazoles; D007931:Leucyl Aminopeptidase; D010455:Peptides; D004364:Pharmaceutical Preparations; D011506:Proteins; D012710:Serum Albumin, Bovine; D014867:Water; D001616:beta-Galactosidase; C507198:cucurbit(8)uril; D047028:Macrocyclic Compounds; D000099246:Cucurbit(n)urils
circular dichroism; cucurbiturils; dyes; macrocycles; sequence recognition; supramolecular chemistry