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Biocatalyzed Dynamic Systemic Domino Thia-Michael--Henry Resolution to Substituted Asymmetric Thiolanes
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
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(English)Article in journal (Other academic) Submitted
Abstract [en]

Dynamic systems based on consecutive thia-Michael and Henry reactions were generated and transformed using lipase-catalyzed asymmetric transformation. Substituted thiolane structures with three contiguous stereocenters were resolved in the process in high yields and high enantiomeric excesses.

National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:kth:diva-123669OAI: oai:DiVA.org:kth-123669DiVA: diva2:628455
Note

QS 2013

Available from: 2013-06-14 Created: 2013-06-14 Last updated: 2013-06-14Bibliographically approved
In thesis
1. Chemoenzymatic Resolution in Dynamic Systems: Screening, Classification and Asymmetric Synthesis
Open this publication in new window or tab >>Chemoenzymatic Resolution in Dynamic Systems: Screening, Classification and Asymmetric Synthesis
2013 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

This  thesis  is  divided  into  four  parts,  all  centered  around  Constitutional Dynamic  Chemistry  (CDC)  and  Dynamic  Kinetic  Resolution  (DKR)  using biocatalysts for selective transformations, and their applications in screening of bioactive compounds, organic synthesis, and enzyme classification.   

In  part  one,  an  introduction  to  CDC  and  DKR  is  presented,  illustrating  the basic  concepts,  practical  considerations  and  potential  applications  of  such dynamic systems, thus providing the background information for the studies in the following chapters.  

In part two, Dynamic Systemic Resolution (DSR), a concept based on CDC is exemplified.  With  enzyme-catalyzed  transformations  as  external  selection pressure,  optimal  structures  can  be  selected  and  amplified  from  the  system. This  concept  is  expanded  to  various  types  of  dynamic  systems  containing single, double cascade/parallel, and multiple reversible reactions. In addition, the  substrate  selectivity  and  catalytic  promiscuity  of  target  enzymes  are  also investigated.  

In   part   three,   DKR   protocols   using   reversible   reactions   for   substrate racemizations  are  illustrated.  Biocatalysts  are  here  employed  for  asymmetric transformations,  resulting  in  efficient  synthetic  pathways  for  enantioenriched organic compounds.  

Part  four  demonstrates  two  unique  applications  of  CDC:  one  resulting  in enzyme  classification  by  use  of  pattern  recognition  methodology;  the  other involving  enzyme  self-inhibition  through  in  situ  transformation  of  stealth inhibitors employing the catalytic activity of the target enzyme.

Place, publisher, year, edition, pages
Stockholm: KTH Royal Institute of Technology, 2013. 71 p.
Series
Trita-CHE-Report, ISSN 1654-1081 ; 2013:29
Keyword
constitutional dynamic chemistry, dynamic systemic resolution, dynamic kinetic resolution, enzyme catalysis, transesterification, enzyme promiscuity, asymmetric synthesis, pattern recognition, self-inhibition.
National Category
Organic Chemistry
Identifiers
urn:nbn:se:kth:diva-123089 (URN)978-91-7501-804-1 (ISBN)
Public defence
2013-08-23, F3, Lindstedtsvägen 26, KTH, Stockholm, 10:00 (English)
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Supervisors
Note

QC 20130614

Available from: 2013-06-14 Created: 2013-05-31 Last updated: 2013-06-14Bibliographically approved

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