Abstract
The structural preferences of furanic compounds were studied using a combination of a molecularly imprinted film (MIF) on a piezoelectric-quartz chip. The furanic compounds and their derivatives were used as the templates. Owing to their similar heterocyclic structures, it is difficult to verify the structural differences between the templates. Therefore, a new cross-linker (Methacr-l-Cys-NHBn)2, was employed to generate a platform on a quartz crystal microbalance (QCM) chip. The cross-linker self-assembled to link the surface of the chip to copolymerize with other functional monomers. A layered film with chiral hydrophobicity and rigidity was thus fabricated. Subsequently, Acr-l-Ser-NHBn was utilized as a chiral monomer to construct MIF on a QCM chip. Forcomparison, we synthesized a more hydrophobic monomer, Methacr-l-Ser-NHBn, to enhance the binding ability of the MIF. The QCM flow injection system was handled in an organic solvent system. The proportion of the monomers was adjusted to optimize the recognition ability of these films. As the binding ability of the MIF toward model templates and structurally-related furanic compounds was improved, a MIF derived from 2-furaldehyde (FUL) achieved a lower detection limit (10 ng/mL). The binding properties of MIFs prepared against furanic compounds exhibited strong similarities to the binding properties of other compounds with heterocyclic ring structures. For example, 2-furaldehyde is very similar to 2-formylthiazole, 2-acetylfuran is similar to 2-acetylthiazole, and 2-furfuryl alcohol is similar to imidazole-2-methanol. Such recognition ability can help distinguish between the structural counterparts of other small heterocyclic compounds.
Highlights
Biological systems use binding modularity to achieve high selectivity, which is an important outcome in synthetic chemistry [1]
Because furanic compounds could be destroyed at high temperatures or high energy conditions, BzH, a planar electrophile with an aromatic skeleton, was chosen as a pseudotemplate to construct MIFBzH -quartz crystal microbalance (QCM) for detecting FUL
Kd value of our target MIFFUL -QCM chip was calculated to be 170 nM; the Kd value of the MIFFTh -QCM chip was 1.87 × nM; and the Kd value of the MIFFIm -QCM chip was 2.12 × nM (Figure 3b). These results strongly suggest that the MIFFUL -QCM chip possesses the most efficient means for discriminating among the targets
Summary
Biological systems use binding modularity to achieve high selectivity, which is an important outcome in synthetic chemistry [1]. Structure-based design is perhaps the most elegant approach to discovering biomimetic compounds that exhibit high specificity and efficiency. MIF-QCM sensors to enable the performance of recognition and discriminating functions, which are helpful in the design, synthesis, and testing of molecular assemblies via the fabrication of biomimetic structures is a very successful approach [7,11,12]. MIF will present a significant imprinting effect via frequency changes In this regard, it is becoming popular to analyze furanic compounds derived from sugars in the food industry [15,16]. MIFQCM sensors offer a means of producing adducts that enable small molecules to bind to one another [15,16,20] to select a suitable model template for a large molecule, which has usually been available based on X-ray scattering structure in the past [21,22,23,24]. The presence of the chiral center on the MIF helps to produce the exact orientation of the hydrogen bonding
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