Sinteza aminalov na osnovi fenilalanina

Schweiger, Matevž (avtor), Grošelj, Uroš (mentor)

L-fenilalanin sem v treh stopnjah pretvoril v terc-butil (S)-butil(1-((2-cikloheptiletil)amino)-1-okso-fenilpropan-2-il)karbamat, iz katerega sem izhajal v nadaljnjih sintezah. Karbamat sem nato nadalje na dva načina skušal pretvoriti v ciklični petčlenski aminal za sintezo prekurzorjev N-heterocikličnih karbenov. Prva pot je vključevala direktno ciklizacijo/redukcijo, druga pa ciklizacijo z močno bazo in sledečo redukcijo nastalega hidantoina. Izhodnemu karbamatu sem odstranil tudi Boc zaščitno skupino in tako pripravil amin, ki je analogen že znanemu učinkovitemu triptofanskemu inhibitorju butirilholinesteraze. Inhibitorno aktivnost amina smo preverili na encimu humane butirilholinesteraze (hBChE).

• Jezik: Slovenski jezik
• Ključne besede: aminal, N-heterociklični karben, butirilholinesteraza, fenilalanin
• Vrsta gradiva: Diplomsko delo/naloga
• Tipologija: 2.11 - Diplomsko delo
• Organizacija: FKKT - Fakulteta za kemijo in kemijsko tehnologijo
• Leto izida: 2019
• PID: 20.500.12556/RUL-108935
• COBISS.SI-ID: 1538294723
• Datum objave v RUL: 08.08.2019

SCHWEIGER, Matevž, 2019, Sinteza aminalov na osnovi fenilalanina [na spletu]. Diplomsko delo. [Dostopano 19 maj 2025]. Pridobljeno s: https://repozitorij.uni-lj.si/IzpisGradiva.php?lang=slv&id=108935

Sekundarni jezik

• Jezik: Angleški jezik
• Naslov: Phenylalanine based aminal synthesis

Izvleček

L-phenylalanine was transformed in three steps into tert-butyl (S)-butyl(1-((2-cycloheptylethyl)amino)-1-oxo-phenylpropane-2-yl)carbamate, which was utilized in further syntheses. Two different approaches were tried in order to convert the carbamate into a cyclic five-membered aminal for the synthesis of precursors to N-heterocyclic carbenes. The first route involved direct cyclization/reduction and the second one cyclization with a strong base and subsequent reduction of the resulting hydantoin. The Boc protecting groups from the starting carbamate was also removed to give an amine analogous to the already known efficient tryptophan-based butyrylcholinesterase inhibitor. The inhibitory activity of the amine has been tested on human butyrylcholinesterase (hBChE). Keywords: aminal, N-heterocyclic carbene, butyrylcholinesterase, phenylalanine

• Ključne besede: aminal, N-heterocyclic carbene, butyrylcholinesterase, phenylalanine