Heterogeneous catalysis in racemization and kinetic resolution along a journey in protein engineering

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Fältnamn	Indikatorer	Metadata
000		04036nam a2200421 4500
001		oai:DiVA.org:su-153921
003		SwePub
008		180308s2018 \| \|\|\|\|\|\|\|\|\|\|\|000 \|\|eng\|
020		a 9789177971856q print
020		a 9789177971863q electronic
024	7	a https://urn.kb.se/resolve?urn=urn:nbn:se:su:diva-1539212 URI
040		a (SwePub)su
041		a engb eng
042		9 SwePub
072	7	a vet2 swepub-contenttype
072	7	a dok2 swepub-publicationtype
100	1	a Görbe, Tamás,d 1988-u Stockholms universitet,Institutionen för organisk kemi4 aut0 (Swepub:su)tmgo8212
245	1 0	a Heterogeneous catalysis in racemization and kinetic resolution along a journey in protein engineering
264	1	a Stockholm :b Department of Organic Chemistry, Stockholm University,c 2018
300		a 81 s.
338		a electronic2 rdacarrier
500		a At the time of the doctoral defense, the following papers were unpublished and had a status as follows: Paper 4: Manuscript. Paper 6: Manuscript.
520		a The first part of my thesis concerns the use of heterogeneous acidic resins for racemization of tert-alcohols without any side-product formation. The focus was to develop a system which can be further extended to a DKR protocol consisting of an enzymatic KR reaction. Based on our knowledge of the resins, an unexpected migratory DKR protocol turned out to be an efficient method for the synthesis of carbocyclic allylic carbinols.The development of enzyme and metal catalyst hybrids was already an ongoing theme in our group. A supporter-free biohybrid catalyst was developed which can be used in several different types of reactions. The Pd(0)-CalB CLEA catalyst was applied in a two-step-cascade transformation and in the DKR of benzylic primary amines. The catalyst was characterized by different analytical techniques, to understand its composition and structure.The enzymes have always been the main focus of the studies and therefore wild type enzymes were initially utilized. However, these natural biocatalysts are associated with certain limitations. In contrast, protein engineering allows for enzymes to be modified and optimized. We have used the technique to create a subtilisin Carlsberg mutant, which was studied both by modeling and in vitro. The mutant was found to catalyze the (S)-selective transesterification of sec-alcohols containing long aliphatic carbon chains, and it also exhibited higher performance in organic solvent.The last project concerned the protein engineering of CalA enzyme towards tert-alcohols. The kinetic resolution of tert-alcohols with this enzyme is very slow but it occurs with good enantioselectivity. The aim was therefore to improve the activity of CalA via protein engineering. Seven amino acids were mutated close to the active site and a library was created based on our prediction. Throughout the screening, a few variants showed higher activity, which were sequenced and further analyzed in the transesterification of tert-alcohols.
650	7	a NATURVETENSKAPx Kemix Organisk kemi0 (SwePub)104052 hsv//swe
650	7	a NATURAL SCIENCESx Chemical Sciencesx Organic Chemistry0 (SwePub)104052 hsv//eng
653		a racemization
653		a protein engineering
653		a kinetic resolution
653		a heterogeneous catalysis
653		a biohybrid catalyst
653		a organisk kemi
653		a Organic Chemistry
700	1	a Bäckvall, Jan-Erling,c Professoru Stockholms universitet,Institutionen för organisk kemi4 ths
700	1	a Hollmann, Frank,c Associate Professoru Department of Biotechnology, Delft University of Technology, The Netherlands4 opn
710	2	a Stockholms universitetb Institutionen för organisk kemi4 org
856	4	u https://su.diva-portal.org/smash/get/diva2:1188639/PREVIEW01.jpgx Previewy preview image
856	4	u https://su.diva-portal.org/smash/get/diva2:1188639/FULLTEXT01.pdfx primaryx Raw objecty fulltext
856	4 8	u https://urn.kb.se/resolve?urn=urn:nbn:se:su:diva-153921

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