Abstract
A novel synthetic N-(9-fluorenyl methoxy carbonyl)-L-Cysteine (Fmoc-Cys(SH)-OH) receptor was pre- pared by co-polymerizing (9-fluorenyl methoxy carbonyl)-S-(1-propene-2-thiol)-L-Cysteine (Fmoc-Cys(SCH2CHCH2)-OH) and a non-imprinted polymer prepared from 1-propene-1-thiol photo-chemically 15 h at room temperature and additional 3 h thermally at 80℃. Subsequently, disulfides were reduced with lithium aluminum hydride (LiAlH4) from imprinted polymers. The imprinted polymers selectively recognized Fmoc-Cys(SH)-OH with high binding constants in aqueous and protic solvents by thiol-disulfide exchange reactions. In order to estimate the covalent rebinding, particles were further extracted and disulfides reduced were estimated with the non-covalent recognized and covalently bounded analytes. From rebinding studies that were conducted, we observed that proved polymer particles could be reproducible and contain constant binding strengths and recognition properties. Furthermore, we proved that short incubation periods resulted in fast and efficient thiol-disulfide interchange reactions.
Highlights
The dynamic nature of receptor recognizes the variety of ligands with multiple non-covalent interactions, andHow to cite this paper: Burri, H.V.R. and Yu, D.H. (2015) An Assay Study of Molecular Recognition of Amino Acids in Water: Covalent Imprinting of Cysteine
Tetrahydrofuran (THF), methanol (MeOH), trifluoroacetic acid (TFA), N,N-Diisopropylethylamine (DIPEA) and piperidine were purchased from Sigma-Aldrich GmBH (Germany); 1-propene-2-thiol, 2,2’-azo-bis(iso-butyronitrile) (AIBN) and N,N-dimethyl formamide (DMF) from Fluka analytical (Buchs, Switzerland); 2M Lithium aluminum hydride solution in THF, ethylene glycol dimethacrylate (EGDMA) and triisopropylsilane (TIS) purchased from Aldrich chemie (Germany)
The binding and selectivity experiments of molecularly imprinted polymers (MIP) and NIPs were performed with batch-wise incubations and MeOH used as a solvent for Fmoc-Cys(SO3H)-OH
Summary
The dynamic nature of receptor recognizes the variety of ligands with multiple non-covalent interactions, and. In the recent-past, numerous techniques have been reported to make artificial receptors such as cyclodextrins [7], crown ethers [8], cyclophanes [9], coordination complexes [10] and molecularly imprinted polymers (MIP) [11]-[13]. Among these techniques template mediating molecularly imprinting technique is more attractive. The recognition pattern of MIPs is reversible bond formation of guest molecule with the binding sites, either covalent or non-covalent bonds. We have employed a covalent imprinting method to synthesize cystein receptor and recognition carried out covalently by thiol-disulfide exchange reaction. The typical molecular imprinting procedure schematically represented in Scheme 1
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