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Preparation of myo-inositol derivatives
Kurčina, Adam ; Kamlar, Martin (advisor) ; Baszczyňski, Ondřej (referee)
Phosphoinositides are naturally occurring molecules with vast range of biological activity important for cell life and survival. The exact role and mechanism of phosphatidylinositol 4,5-bisphosphate's actions are not yet elucidated. This bachelor's thesis is dedicated to the synthesis of selectively protected myo-inositol derivative suitable as precursor for synthesis of phosphatidylinositol 4,5-bisphosphate derivatives. Key words: Inositol, protective groups, regioisomers
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Selective protection of pentaerythrityltetraamine
Mangl, Ondřej ; Hermann, Petr (advisor) ; Kotek, Jan (referee)
Selective protection of functional groups is a commonly used method which is used in multistep synthesis. Pentaerythrityltetraamine (PEA) is substance with four amino groups and substances with one to three selectively protected amino groups were prepared. Protections by t-butyloxycarbonyl (Boc) which is stable under neutral and basic conditions and can be deprotected in the acidic conditions, and with benzyloxycarbonyl (Cbz) which is stable under acidic and basic conditions and can be eliminated by hydrogenation was tested. Separation and purification of the protected amines was done by chromatography. Selectively protected PEA can be also prepared by indirect path by stepwise reduction of pentaerythrityltetraazide. Pentaerythritylmonoamine-triazide is prepared two-phase reduction and the amino group of the monoamine is protected with Boc or Cbz.
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Construction of modified DNAs with selected reactive or protective groups
Vaníková, Zuzana ; Hocek, Michal (advisor) ; Křen, Vladimír (referee) ; Zimčík, Petr (referee)
This PhD thesis is focused on the synthesis of DNA modified with photocleavable 2- nitrobenzyl protecting groups in major groove and its applications in the regulation of gene expression in the level of transcription. In the first part of my thesis, the synthesis of photocaged 2'-deoxyribonucleosides triphosphates and their photolysis to unprotected 5-hydroxymethylated nucleotides is described. All prepared nucleoside triphosphates were good substrates for their enzymatic incorporation into DNA. Synthesized 5-(2-nitrobenzyloxy)methyl-2'-deoxyuridine-5'- monophosphate (dUNBMP) and DNA with one 5-(2-nitrobenzyloxy)methyl- modification in the sequence were used for the detailed kinetic studies of photocleavage reactions. In the second part of the thesis, the series of modified DNAs with specific sequences were prepared by primer extension (PEX) and/or polymerase chain reaction (PCR). A cleavage of prepared modified DNAs was studied by selected restriction endonucleases (REs). In all cases, the nitrobenzylated DNA fully resist the cleavage by REs. The deprotection/ photocleavage conditions for nitrobenzylated DNA were studied in the case of DNAs with positive restriction endonuclease digestion of hydroxymethylated DNA. The resulting photocleaved DNA was fully digested by REs, therefore 2-nitrobenzyl...
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Selective protection of pentaerythrityltetraamine
Mangl, Ondřej ; Hermann, Petr (advisor) ; Kotek, Jan (referee)
Selective protection of functional groups is a commonly used method which is used in multistep synthesis. Pentaerythrityltetraamine (PEA) is substance with four amino groups and substances with one to three selectively protected amino groups were prepared. Protections by t-butyloxycarbonyl (Boc) which is stable under neutral and basic conditions and can be deprotected in the acidic conditions, and with benzyloxycarbonyl (Cbz) which is stable under acidic and basic conditions and can be eliminated by hydrogenation was tested. Separation and purification of the protected amines was done by chromatography. Selectively protected PEA can be also prepared by indirect path by stepwise reduction of pentaerythrityltetraazide. Pentaerythritylmonoamine-triazide is prepared two-phase reduction and the amino group of the monoamine is protected with Boc or Cbz.
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