Ändra sökning
RefereraExporteraLänk till posten
Permanent länk

Direktlänk
Referera
Referensformat
  • apa
  • harvard1
  • ieee
  • modern-language-association-8th-edition
  • vancouver
  • Annat format
Fler format
Språk
  • de-DE
  • en-GB
  • en-US
  • fi-FI
  • nn-NO
  • nn-NB
  • sv-SE
  • Annat språk
Fler språk
Utmatningsformat
  • html
  • text
  • asciidoc
  • rtf
Double parallel dynamic resolution through lipase-catalyzed asymmetric transformation
KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
2013 (Engelska)Ingår i: Chemical Communications, ISSN 1359-7345, E-ISSN 1364-548X, Vol. 49, nr 18, s. 1805-1807Artikel i tidskrift (Refereegranskat) 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.

Ort, förlag, år, upplaga, sidor
RSC Publishing, 2013. Vol. 49, nr 18, s. 1805-1807
Nationell ämneskategori
Organisk kemi
Identifikatorer
URN: urn:nbn:se:kth:diva-119127DOI: 10.1039/c3cc38203fISI: 000314650100006Scopus ID: 2-s2.0-84873606019OAI: oai:DiVA.org:kth-119127DiVA, id: diva2:610407
Forskningsfinansiär
Vetenskapsrådet
Anmärkning

QC 20130311

Tillgänglig från: 2013-03-11 Skapad: 2013-03-07 Senast uppdaterad: 2017-12-06Bibliografiskt granskad
Ingår i avhandling
1. Chemoenzymatic Resolution in Dynamic Systems: Screening, Classification and Asymmetric Synthesis
Öppna denna publikation i ny flik eller fönster >>Chemoenzymatic Resolution in Dynamic Systems: Screening, Classification and Asymmetric Synthesis
2013 (Engelska)Doktorsavhandling, sammanläggning (Övrigt vetenskapligt)
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.

Ort, förlag, år, upplaga, sidor
Stockholm: KTH Royal Institute of Technology, 2013. s. 71
Serie
Trita-CHE-Report, ISSN 1654-1081 ; 2013:29
Nyckelord
constitutional dynamic chemistry, dynamic systemic resolution, dynamic kinetic resolution, enzyme catalysis, transesterification, enzyme promiscuity, asymmetric synthesis, pattern recognition, self-inhibition.
Nationell ämneskategori
Organisk kemi
Identifikatorer
urn:nbn:se:kth:diva-123089 (URN)978-91-7501-804-1 (ISBN)
Disputation
2013-08-23, F3, Lindstedtsvägen 26, KTH, Stockholm, 10:00 (Engelska)
Opponent
Handledare
Anmärkning

QC 20130614

Tillgänglig från: 2013-06-14 Skapad: 2013-05-31 Senast uppdaterad: 2013-06-14Bibliografiskt granskad
2. Resolution of Dynamic Systems: Applications in Asymmetric Synthesis and Materials Science
Öppna denna publikation i ny flik eller fönster >>Resolution of Dynamic Systems: Applications in Asymmetric Synthesis and Materials Science
2014 (Engelska)Doktorsavhandling, sammanläggning (Övrigt vetenskapligt)
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.

Ort, förlag, år, upplaga, sidor
Stockholm: KTH Royal Institute of Technology, 2014. s. 63
Serie
TRITA-CHE-Report, ISSN 1654-1081 ; 2014:34
Nationell ämneskategori
Organisk kemi
Forskningsämne
Kemi
Identifikatorer
urn:nbn:se:kth:diva-151314 (URN)978-91-7595-239-0 (ISBN)
Disputation
2014-10-10, F3, Lindstedtsvägen 26, KTH, Stockholm, 14:00 (Engelska)
Opponent
Handledare
Forskningsfinansiär
Vetenskapsrådet, KDHH B60940
Anmärkning

QC 20140918

Tillgänglig från: 2014-09-18 Skapad: 2014-09-17 Senast uppdaterad: 2014-09-18Bibliografiskt granskad

Open Access i DiVA

Fulltext saknas i DiVA

Övriga länkar

Förlagets fulltextScopusPublished version freely available

Sök vidare i DiVA

Av författaren/redaktören
Zhang, YanHu, LeiRamström, Olof
Av organisationen
Organisk kemi
I samma tidskrift
Chemical Communications
Organisk kemi

Sök vidare utanför DiVA

GoogleGoogle Scholar

doi
urn-nbn

Altmetricpoäng

doi
urn-nbn
Totalt: 65 träffar
RefereraExporteraLänk till posten
Permanent länk

Direktlänk
Referera
Referensformat
  • apa
  • harvard1
  • ieee
  • modern-language-association-8th-edition
  • vancouver
  • Annat format
Fler format
Språk
  • de-DE
  • en-GB
  • en-US
  • fi-FI
  • nn-NO
  • nn-NB
  • sv-SE
  • Annat språk
Fler språk
Utmatningsformat
  • html
  • text
  • asciidoc
  • rtf