diplomsko delo
Doroteja Lipovec (Author), Jurij Svete (Mentor)

Abstract

Biološke sonde oziroma 'acivity-based probes' so male molekule, ki se ireverzibilno vežejo na aktivno mesto proteaze. Vsebujejo reaktivno elektrofilno skupino ("bojno glavo"), ki reagira z aktivnim mestom preiskovanega encima, in označevalec; povezuje pa ju distančnik, ki z ustreznim aminokislinskim zaporedjem poveča selektivnost sonde. Diazoketon (Nα-benziloksikarbonil-Nβ-terc-butoksikarbonil-3,7-diamino-1-diazo-2-oksoheptan) smo sintetizirali iz Z-Lys(Boc)-OH po že znanem postopku iz literature. Iz diazoketona smo sintetizirali aciloksimetil keton (AOMK) (Nα-benziloksikarbonil-Nβ-terc-butoksikarbonil-3,7-diamino-2-oksoheptil 2,6-dimetilbenzoat) po različnih poteh. AOMK smo najprej sintetizirali z direktno sintezo med diazoketonom in 2,6-dimetilbenzojsko kislino v fluoriranem alkoholu (TFE). Zatem smo AOMK želeli sintetizirati preko p-tozilatnega derivata, ki pa je razpadel, zato je bila sinteza neuspešna. AOMK smo nato sintetizirali preko klorometil ketona po modificiranem postopku iz literature.

Keywords

biološke sonde;elektrofilne bojne glave;aciloksimetil ketoni;diazoketoni;kaspaze;diplomska dela;

Data

Language: Slovenian
Year of publishing:
Typology: 2.11 - Undergraduate Thesis
Organization: UL FKKT - Faculty of Chemistry and Chemical Technology
Publisher: [D. Lipovec]
UDC: 547.1.057(043.2)
COBISS: 128970755 Link will open in a new window
Views: 70
Downloads: 26
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Other data

Secondary language: English
Secondary title: Synthesis and transformation of Nα-benzyloxycarbonyl-Nβ-tert-butoxycarbonyl-3,7-diamino-1-diazo-2-oxoheptane
Secondary abstract: Activity-based probes are small molecules that bind specifically and irreversibly to active proteases. They consist of a reactive functional group (“electrophilic warhead”) that binds to the active site of the target enzyme, a tag that enables enzyme detection, and a linker that is a peptide based sequence that connects the warhead with the tag and provides the selectivity towards an enzyme of interest. Diazoketone (Nα-benzyloxycarbonyl-Nβ-tert-butoxycarbonyl-3,7-diamino-1-diazo-2-oxoheptane) was synthesized from Z-Lys(Boc)-OH following a procedure described in the literature. Acyloxymethyl ketone (AOMK) (Nα-benzyloxycarbonyl-Nβ-tert-butoxycarbonyl-3,7-diamino-2-oxoheptyl 2,6-dimethylbenzoate) was then synthesized from the diazoketone using different methods. AOMK was first synthesized via direct substitution reaction between the diazoketone and 2,6-dimethylbenzoic acid in a fluorinated solvent (TFE). Synthesis of AOMK through the p-tosylate derivative was unsuccessful as the derivative decomposed. AOMK was then synthesized through a chloromethyl ketone according to a modified literature procedure.
Secondary keywords: activity-based probes;electrophilic warheads;acyloxymethyl ketones;diazoketones;caspases;Organska sinteza (kemija);Univerzitetna in visokošolska dela;
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: 45 str.
ID: 16411125