Sinteza aminalov na osnovi fenilalanina

diplomsko delo

Matevž Schweiger (Author), Uroš Grošelj (Mentor)

Abstract

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).

Keywords

organska kemija;organska sinteza;N-heterociklični karbeni;aminal;butirilholinesteraza;fenilalanin;diplomska dela;

Data

Language:	Slovenian
Year of publishing:	2019
Typology:	2.11 - Undergraduate Thesis
Organization:	UL FKKT - Faculty of Chemistry and Chemical Technology
Publisher:	[M. Schweiger]
UDC:	547.7.057(043.2)
COBISS:	1538294723
Views:	806
Downloads:	252
Average score:	0 (0 votes)
Metadata:

Other data

Secondary language:	English
Secondary title:	Phenylalanine based aminal synthesis
Secondary abstract:	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
Secondary keywords:	aminal;N-heterocyclic carbene;butyrylcholinesterase;phenylalanine;
Type (COBISS):	Bachelor thesis/paper
Study programme:	1000373
Embargo end date (OpenAIRE):	1970-01-01
Thesis comment:	Univ. v Ljubljani, Fak. za kemijo in kemijsko tehnologijo, UNI Kemija
Pages:	34 str.
ID:	11199165