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Chemoenzymatic Appr...
Chemoenzymatic Approaches to the Synthesis of the Calcimimetic Agent Cinacalcet Employing Transaminases and Ketoreductases
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- Marx, Lisa (author)
- KTH,Industriell bioteknologi
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Rios-Lombardia, Nicolas (author)
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Farnberger, Judith F. (author)
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Kroutil, Wolfgang (author)
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Benitez-Mateos, Ana I. (author)
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Lopez-Gallego, Fernando (author)
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Moris, Francisco (author)
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Gonzalez-Sabin, Javier (author)
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- Berglund, Per (author)
- KTH,Industriell bioteknologi
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(creator_code:org_t)
- 2018-02-28
- 2018
- English.
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In: Advanced Synthesis and Catalysis. - : Wiley-VCH Verlagsgesellschaft. - 1615-4150 .- 1615-4169. ; 360:11, s. 2157-2165
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Abstract
Subject headings
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- Abstract Several chemoenzymatic routes have been explored for the preparation of cinacalcet, a calcimimetic agent. Transaminases (TAs) and ketoreductases (KREDs) turned out to be useful biocatalysts for the preparation of key optically active precursors. Thus, the asymmetric amination of 1âacetonaphthone yielded an enantiopure (R)âamine, which can be alkylated in one step to yield cinacalcet. Alternatively, the bioreduction of the same ketone resulted in an enantiopure (S)âalcohol, which was easily converted into the previous (R)âamine. In addition, the reduction was efficiently performed with the KRED and its cofactor coâimmobilized on the same porous surface. This selfâsufficient heterogeneous biocatalyst presented an accumulated total turnover number (TTN) for the cofactor of 675 after 5 consecutive operational cycles. Finally, in a preparative scale synthesis the TAâbased approach was performed in aqueous medium and led to enantiopure cinacalcet in two steps and 50% overall yield.
Subject headings
- TEKNIK OCH TEKNOLOGIER -- Industriell bioteknik -- Biokatalys och enzymteknik (hsv//swe)
- ENGINEERING AND TECHNOLOGY -- Industrial Biotechnology -- Biocatalysis and Enzyme Technology (hsv//eng)
Keyword
- Cinacalcet
- Transaminases
- Ketoreductases
- Asymmetric synthesis
- Biocatalysis
- Bioteknologi
- Biotechnology
Publication and Content Type
- ref (subject category)
- art (subject category)
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