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Double parallel dynamic resolution through lipase-catalyzed asymmetric transformation
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.
2013 (English)In: Chemical Communications, ISSN 1359-7345, E-ISSN 1364-548X, Vol. 49, no 18, 1805-1807 p.Article in journal (Refereed) Published
Abstract [en]

Dynamic systems based on double parallel reactions have been generated and resolved in situ by secondary lipase-catalyzed asymmetric transformation, resulting in high chemo- and enantioselectivities.

Place, publisher, year, edition, pages
RSC Publishing, 2013. Vol. 49, no 18, 1805-1807 p.
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:kth:diva-119127DOI: 10.1039/c3cc38203fISI: 000314650100006Scopus ID: 2-s2.0-84873606019OAI: oai:DiVA.org:kth-119127DiVA: diva2:610407
Funder
Swedish Research Council
Note

QC 20130311

Available from: 2013-03-11 Created: 2013-03-07 Last updated: 2017-12-06Bibliographically 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)
Opponent
Supervisors
Note

QC 20130614

Available from: 2013-06-14 Created: 2013-05-31 Last updated: 2013-06-14Bibliographically approved
2. Resolution of Dynamic Systems: Applications in Asymmetric Synthesis and Materials Science
Open this publication in new window or tab >>Resolution of Dynamic Systems: Applications in Asymmetric Synthesis and Materials Science
2014 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

This thesis is built on the concepts of constitutional dynamic chemistry and dynamic kinetic resolution, where reversible covalent reactions are used to generate dynamics and kinetically controlled reactions are employed for resolution. The thesis is divided into two parts:

The first section focuses on the study of dynamic systemic resolution, a concept derived from constitutional dynamic chemistry. Three projects are addressed in this section: 1) lipase-catalyzed resolution of a double parallel dynamic system involving both hemiacetal formation and nitroaldol reaction; 2) resolution of a dynamic α-iminonitrile system through a silver-catalyzed 1,3-dipolar cycloaddition process; 3) resolution of a dynamic imine system via organogelation. Both external and internal selection pressures are applied for the resolution of complex dynamic systems.

The second section explores the asymmetric synthesis of two types of heterocycles through dynamic kinetic resolution. In the first example, a series of novel N-, O-, S-containing six-membered oxathiazinanones are obtained through a lipase-mediated dynamic domino nitrone addition-cyclization pathway. In the second example, the anti-HIV nucleoside lamivudine is synthesized through a three-step surfactant-treated subtilisin Carlsberg-catalyzed dynamic kinetic resolution protocol. Its enantiomer is also accessible by changing subtilisin Carlsberg to lipases. In addition, the enzyme selectivity towards the formation of five-membered oxathiolane derivatives is investigated.

Place, publisher, year, edition, pages
Stockholm: KTH Royal Institute of Technology, 2014. 63 p.
Series
TRITA-CHE-Report, ISSN 1654-1081 ; 2014:34
National Category
Organic Chemistry
Research subject
Chemistry
Identifiers
urn:nbn:se:kth:diva-151314 (URN)978-91-7595-239-0 (ISBN)
Public defence
2014-10-10, F3, Lindstedtsvägen 26, KTH, Stockholm, 14:00 (English)
Opponent
Supervisors
Funder
Swedish Research Council, KDHH B60940
Note

QC 20140918

Available from: 2014-09-18 Created: 2014-09-17 Last updated: 2014-09-18Bibliographically approved

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