Covalent Imprinting of Silica Networks via so-gel processing
Translated title
Kovalent Prægning af Silikanetværk via sol-gel processen
Author
Nielsen, Erik
Term
4. term
Education
Publication year
2010
Abstract
This thesis investigates whether silica networks can be covalently imprinted via the sol-gel process to achieve selective molecular recognition in mechanically robust materials suitable for HPLC column packings. The rationale is that molecularly imprinted materials offer high selectivity, while silica derived from TEOS under mild conditions provides a durable, tunable support. The study employs disulfide-based covalent imprinting, relevant to recognizing cysteine-containing peptides and proteins; for reliable UV detection by HPLC, benzyl thiosulfate (BT) is used as the template. Three covalently imprinted silica networks (CISs) are synthesized with different ratios of cross-linker to functional monomer, and three non-imprinted silica networks (NISs) are prepared using the same sol-gel protocol with 3-mercaptopropyltrimethoxysilane in place of the functional monomer. Selectivity and rebinding are assessed by batch rebinding experiments using four structurally related guests: BT (template), 4-tert-butylbenzyl thiosulfate (TBT), benzyl alcohol (BA), and benzyl mercaptan (BM), quantified by HPLC-UV. The thesis also outlines relevant sol-gel chemistry (hydrolysis/condensation, acid/base catalysis) and binding isotherms used for characterization. Results, including CIS versus NIS comparisons and the influence of cross-link density on binding behavior, are presented in the full thesis.
Dette speciale undersøger, om silikanetværk kan kovalent prægnes via sol-gel-processen for at opnå selektiv molekylgenkendelse i mekanisk stabile materialer egnet til HPLC-kolonnepakninger. Baggrunden er, at molekylært prægede materialer kan give høj selektivitet, og at silika, fremstillet fra TEOS under milde betingelser, er et robust og kemisk modificerbart bæremateriale. Projektet fokuserer på disulfidbaseret kovalent prægning, som er relevant for genkendelse af cysteinholdige peptider og proteiner; af hensyn til pålidelig UV-detektion i HPLC anvendes benzyl thiosulfate (BT) som skabelon. Der fremstilles tre kovalent prægede silikanetværk (CIS) med varierende forhold mellem krydsbindingsmiddel og funktionel monomer, samt tre ikke-prægede silikanetværk (NIS) syntetiseret efter samme sol-gel-protokol, hvor 3-mercaptopropyltrimethoxysilan erstatter den funktionelle monomer. Selektivitet og genbindingskapacitet undersøges ved batch-genbindingsforsøg med fire gæstemolekyler med beslægtet struktur: BT (skabelon), 4-tert-butylbenzyl thiosulfate (TBT), benzyl alcohol (BA) og benzyl mercaptan (BM), med kvantificering via HPLC-UV. Specialet gennemgår desuden den relevante sol-gel-kemi (hydrolyse/kondensation, syre/base-katalyse) og anvendte bindingsisotermer til karakterisering. Resultater, herunder sammenligning mellem CIS og NIS samt effekten af krydsbindingsgraden på bindingsegenskaber, præsenteres i den fulde afhandling.
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