Selective Recognition of Aromatic Amino Acids by a Molecular Cleft in Water

The development of water‐soluble hosts for the selective recognition of aromatic amino acids is highly desirable and may serve as a tool to facilitate drug discovery and enable fabrication of sensors for point‐of‐care monitoring in the context of phenylketonuria disease. This paper presents the synt...

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Bibliographic Details
Published in:Helvetica chimica acta 2024-02, Vol.107 (2), p.n/a
Main Authors: Keller, Joël F., Valášek, Michal, Mayor, Marcel
Format: Article
Language:English
Subjects:
Amino acids
Aqueous solutions
Calorimetry
Fabrication
host-guest systems
molecular recognition
NMR
Nuclear magnetic resonance
Phenylketonuria
receptors
Recognition
Titration
Titration calorimetry
water chemistry
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Summary:The development of water‐soluble hosts for the selective recognition of aromatic amino acids is highly desirable and may serve as a tool to facilitate drug discovery and enable fabrication of sensors for point‐of‐care monitoring in the context of phenylketonuria disease. This paper presents the synthesis and characterization of a water‐soluble molecular cleft which is demonstrated to selectively bind aromatic amino acid guests over other amino acids in aqueous medium, favoring ʟ‐Trp over ʟ‐Phe and ʟ‐Tyr by a factor of approximately five. Host/guest‐interaction forces were studied by 1H‐NMR titrations complemented by fluorescence titrations and isothermal titration calorimetry. The here presented results provide a starting point for future optimizations in our efforts to selectively identify and quantify individual aromatic amino acids in aqueous medium.
ISSN:0018-019X
1522-2675
DOI:10.1002/hlca.202300221