Sinteza cijanoalkohola katalizirana halogenhidrin-dehalogenazom

master's thesis

• Title (english): Synthesis of cyano-alcohol catalysed by halohydrin dehalogenase
• Author: Lorena Mateša
• Mentor: Zvjezdana Findrik Blažević (mentor)
• Committee member: Zvjezdana Findrik Blažević (predsjednik povjerenstva)
• Committee member: Martina Sudar (član povjerenstva)
• Committee member: Marija Vuković Domanovac (član povjerenstva)
• Granter: University of Zagreb; Faculty of Chemical Engineering and Technology; Zagreb
• Defense date and country: 2021-06-21, Croatia
• Scientific / art field, discipline and subdiscipline: TECHNICAL SCIENCES; Chemical Engineering

Abstract

Enzimi su biokatalizatori prisutni u mikroorganizmima, a djeluju poput anorganskih katalizatora. Njihova uporaba osigurava niz prednosti, poput odvijanja reakcija u blažim uvjetima te smanjenje nastanka štetnih nusprodukata. Halogenhidrin-dehalogenaze su enzimi koji kataliziraju reakciju dehalogenacije haloalkohola uz stvaranje epoksida, kao i reverzibilnu reakciju, reakciju otvaranja epoksidnog prstena s nukleofilima. U ovom je radu ispitana reakcija otvaranja epoksidnog prstena 2-(4-trifluormetil)fenil oksirana, kataliziranu C tipom halogenhidrin-dehalogenaze HheC-W249P uz natrijev cijanid kao nukleofil, u kotlastom reaktoru i mikroreaktoru. Reakcija je praćena uporabom HPLC analize, a aktivnost enzima je praćena spektrofotometrijski. Osim reakcije otvaranja epoksidnog prstena, istraživane su i reakcija hidrolize epoksida i kemijska reakcija otvaranja epoksidnog prstena. Reakciju je moguće provesti i u kotlastom reaktoru i u mikroreaktoru. U kotlastom reaktoru količina nastalog produkta se povećava s vremenom odvijanja reakcije. U mikroreaktoru, najviše produkta nastane pri najvećem vremenu zadržavanja, ali tada se epoksid troši i sporednim reakcijama. Brzina deaktivacije enzima se povećava porastom prostornog vremena zadržavanja.

Abstract (english)

Enzymes are biocatalysts present in microorganisms and act like inorganic catalysts. Their usage provides a number of benefits, such as reactions in milder conditions and a reduction in occurence of harmful by.products. Halohydrin dehalogenases are enzymes that catalyze dehalogenation od haloalcohols to form epoxides, as well as the reversible reaction, the ring-opening reaction with nucleophiles. In this work, the ring-opening reaction of
2-(4-trifluormethyl)phenyl oxirane with sodium cyanide as nucleophile, catalyzed by C-type halohydrin dehalogenase HheC-W249P, in batch reactor and microreactor,was investigated. The reaction was monitored using HPLC analysis and the enzyme activity was monitored spectrofotometrically. In addition to epoxy ring-opening reaction, the hydrolysis reaction of epoxide and the chemical ring opening reaction of epoxide were also tested. The reaction can be carried out in both the batch reactor and the microreactor. In the batch reactor, the amount of the product formed increases with the reaction time. In the microreactor, the highest amount of product formed was observed at highest retention time, but then the epoxide is consumed in side reactions. Also, enzyme deactivation rate increases with increase of retention times in the microreactor.

• Keywords: biokataliza; enzimi; halogenhidrin-dehalogenaza; mikroreaktori; epoksidi; β-hidroksi nitrili
• Keywords (english): biocatalysis; enzymes; halohydrin dehalogenases; microreactor; epoxides; β-hydroxy nitriles
• Language: croatian
• URN:NBN: urn:nbn:hr:149:352899
• Project: Number: IP-2018-01-4493; Title: Enzimska sinteza fluoriranih kiralnih građevnih blokova; Acronym: EnzyFluor; Leader: Maja Majerić-Elenkov; Jurisdiction: Croatia; Funder: HRZZ; Funding stream: IP
• Study programme: Title: Chemical Engineering - Graduate study; Study programme type: university; Study level: graduate; Academic / professional title: magistar/magistra inženjer/inženjerka kemijskog inženjerstva (magistar/magistra inženjer/inženjerka kemijskog inženjerstva)
• Type of resource: Text
• File origin: Born digital
• Access conditions: Open access; Embargo expiration date: 2022-10-31
• Created on: 2023-04-05 13:30:16