diplomsko delo
Urban Avsec (Author), Jurij Svete (Mentor)

Abstract

V diplomskem delu sem izvedel fotoredoks katalizirane C-H arilacije 1-ciano-4-okso-4H-kinolizin-3-diazonijevega tetrafluoroborata (1) z N-Boc-L-fenilalanin metil estrom (2), N-Boc-L-tirozin metil estrom (3), N-Boc-L-histidin metil estrom (4), N-Boc-L-triptofan metil estrom (5) ter z dinatrijevo soljo eozina Y, kot fotokatalizatorjem. Reakcije so potekale pri sobni temperaturi in pri obsevanju z zeleno svetlobo. Pri vseh reakcijah so nastali predvideni regioizomeri produktov arilacije, pri reakciji s histidinom 4, pa sta nastala tudi azo adukta 4c,d. Dobljene produkte sem delno ločil z bliskovito kolonsko kromatografijo in jih okarakteriziral s 1H in 13C spektroskopijo ter HRMS analizo.

Keywords

biokonjugacija beljakovin;fotoredoks kataliza;diazonijeva sol;aminokislinski derivati;diplomska dela;

Data

Language: Slovenian
Year of publishing:
Typology: 2.11 - Undergraduate Thesis
Organization: UL FKKT - Faculty of Chemistry and Chemical Technology
Publisher: [U. Avsec]
UDC: 547.1:544.526.5(043.2)
COBISS: 247089923 Link will open in a new window
Views: 58
Downloads: 11
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Other data

Secondary language: English
Secondary title: Catalytic photoredox C-H arylation of 1-cyano-4-oxo-4H-quinolizine-3-diazonium tetrafluoroborate with derivatives of aromatic aminoacids
Secondary abstract: In my thesis, I performed photoredox-catalyzed C-H arylations of 1-cyano-4-oxo-4H- quinolizine-3-diazonium tetrafluoroborate (1) with N-Boc-L-phenylalanine methyl ester (2), N-Boc-L-tyrosine methyl ester (3), N-Boc-L-histidine methyl ester (4) and N-Boc-L- tryptophan methyl ester (5) using the disodium salt of eosin Y as the photocatalyst. The reactions were carried out at room temperature and under green light irradiation. All reactions yielded the expected regioisomers of the arylation products, while the reaction with histidine 4 also yielded azo adducts 4c,d. The obtained products were partially separated by flash column chromatography and characterized by 1H and 13C spectroscopy and HRMS analysis.
Secondary keywords: diazonium salt;amino acid derivatives;photoredox catalysis;bioconjugation;Kataliza;Aminokisline;Univerzitetna in visokošolska dela;
Type (COBISS): Bachelor thesis/paper
Study programme: 1000373
Thesis comment: Univ. v Ljubljani, Fak. za kemijo in kemijsko tehnologijo, UNI Kemija
Pages: 1 spletni vir (1 datoteka PDF (54 str.))
ID: 27225088