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Efficient asymmetric synthesis of lamivudine via enzymatic dynamic kinetic resolution
KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.ORCID-id: 0000-0001-5298-4310
KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
2013 (engelsk)Inngår i: Chemical Communications, ISSN 1359-7345, E-ISSN 1364-548X, Vol. 49, nr 88, s. 10376-10378Artikkel i tidsskrift (Fagfellevurdert) Published
Abstract [en]

The anti-HIV nucleoside lamivudine was asymmetrically synthesized in only three steps via a novel surfactant-treated subtilisin Carlsberg-catalyzed dynamic kinetic resolution protocol. The enantiomer of lamivudine could also be accessed using the same protocol catalyzed by Candida antarctica lipase B.

sted, utgiver, år, opplag, sider
2013. Vol. 49, nr 88, s. 10376-10378
Emneord [en]
Potent Antiviral Agent, Secondary Alcohols, Enantioselective Synthesis, Nucleoside Analogs, Organic-Synthesis, Anti-Hiv, Lipase, Replication, Catalysts, 3tc(Tm)
HSV kategori
Identifikatorer
URN: urn:nbn:se:kth:diva-133666DOI: 10.1039/c3cc45551cISI: 000325723900011Scopus ID: 2-s2.0-84885455365OAI: oai:DiVA.org:kth-133666DiVA, id: diva2:662780
Forskningsfinansiär
Swedish Research Council
Merknad

QC 20131108

Tilgjengelig fra: 2013-11-08 Laget: 2013-11-08 Sist oppdatert: 2017-12-06bibliografisk kontrollert
Inngår i avhandling
1. Resolution of Dynamic Systems: Applications in Asymmetric Synthesis and Materials Science
Åpne denne publikasjonen i ny fane eller vindu >>Resolution of Dynamic Systems: Applications in Asymmetric Synthesis and Materials Science
2014 (engelsk)Doktoravhandling, med artikler (Annet vitenskapelig)
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.

sted, utgiver, år, opplag, sider
Stockholm: KTH Royal Institute of Technology, 2014. s. 63
Serie
TRITA-CHE-Report, ISSN 1654-1081 ; 2014:34
HSV kategori
Forskningsprogram
Kemi
Identifikatorer
urn:nbn:se:kth:diva-151314 (URN)978-91-7595-239-0 (ISBN)
Disputas
2014-10-10, F3, Lindstedtsvägen 26, KTH, Stockholm, 14:00 (engelsk)
Opponent
Veileder
Forskningsfinansiär
Swedish Research Council, KDHH B60940
Merknad

QC 20140918

Tilgjengelig fra: 2014-09-18 Laget: 2014-09-17 Sist oppdatert: 2014-09-18bibliografisk kontrollert

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