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Sinteza in karakterizacija nenaravne aminokisline
ID Baša, Jana (Author), ID Gazvoda, Martin (Mentor) More about this mentor... This link opens in a new window, ID Marolt, Gregor (Comentor)

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Abstract
Sinteza nenaravnih aminokislin in njihova vgradnja v proteine je vedno bolj zanimivo in intenzivno področje raziskovanja. Cilj je sintetizirati aminokisline z vgradnjo katerih bomo spremenili lastnosti proteinov in npr. dosegli njihovo večjo stabilnost, funkcionalnost in specifičnost. Cilj diplomskega dela je bila sintetiza nenaravne aminokisline – azahistidina, ki je analog naravnega histidina. Sinteza je potekala z uporabo z bakrom katalizirane reakcije med propargil glicinom in hidrazojsko kislino, ki je pri sintezi nastala in situ med natrijevim azidom in metanojsko kislino. Tako pripravljen azahistidin ima na stranski verigi triazolni obroč, ki med drugim lahko predstavlja koordinativno mesto za kovine. S titracijami (1H-1,2,3-triazola) sem preverjala, katere kovine in v kolikšni meri se lahko potencialno vežejo na triazolni fragment te nenaravne aminokisline. Ugotovili smo, da se na 1H-1,2,3-triazol najboljše vežejo kobaltovi in cinkovi ioni.

Language:Slovenian
Keywords:aminokisline, histidin, triazol, »klik kemija«, potenciometrične titracije
Work type:Bachelor thesis/paper
Typology:2.11 - Undergraduate Thesis
Organization:FKKT - Faculty of Chemistry and Chemical Technology
Year:2024
PID:20.500.12556/RUL-161298 This link opens in a new window
COBISS.SI-ID:214074883 This link opens in a new window
Publication date in RUL:09.09.2024
Views:208
Downloads:78
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Secondary language

Language:English
Title:Synthesis and determination of structural properties of a non-natural amino acid
Abstract:
The synthesis of non-natural amino acids and their incorporation into proteins is an increasingly exciting area of research that is developing rapidly. The aim is to synthesize amino acids whose incorporation into proteins changes their properties, e.g. increases their stability, functionality and specificity. The main objective of this thesis was to synthesise a non-natural amino acid, azahistidine, an analogue of the natural histidine. The synthesis was carried out by a copper-catalysed reaction between propargyl glycine and hydrazoic acid formed in situ during synthesis between sodium azide and methanoic acid. The azahistidine prepared has a triazole ring on the side chain, which, among others, can represent the coordinating site for metals. I performed titrations of 1,2,3-triazole (1H-1,2,3-triazole) to test which metals can bind to the triazole fragment of the non-natural amino acid and to what extent. I found that the 1H-1,2,3-triazole most efficiently binds cobalt and zinc ions.

Keywords:amino acids, histidine, triazole, »click« chemistry, potentiometric titration

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