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Continuous diastereomeric kinetic resolution—silybins a and b
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SYSNO ASEP 0547149 Druh ASEP J - Článek v odborném periodiku Zařazení RIV J - Článek v odborném periodiku Poddruh J Článek ve WOS Název Continuous diastereomeric kinetic resolution—silybins a and b Tvůrce(i) Biedermann, David (MBU-M) RID, ORCID
Hurtová, Martina (MBU-M) ORCID
Benada, Oldřich (MBU-M) ORCID, RID
Valentová, Kateřina (MBU-M) RID, ORCID
Biedermannová, Lada (BTO-N) RID, ORCID
Křen, Vladimír (MBU-M) RID, ORCIDČíslo článku 1106 Zdroj.dok. Catalysts. - : MDPI
Roč. 11, č. 9 (2021)Poč.str. 13 s. Jazyk dok. eng - angličtina Země vyd. CH - Švýcarsko Klíč. slova Silybin ; Silybum marianum ; Silymarin ; milk thistle ; lipase ; Novozym 435 ; diastereomers ; resolution ; flow reaction Vědní obor RIV CC - Organická chemie Obor OECD Organic chemistry Vědní obor RIV – spolupráce Biotechnologický ústav - Organická chemie CEP LTC18071 GA MŠMT - Ministerstvo školství, mládeže a tělovýchovy GA21-00551S GA ČR - Grantová agentura ČR Způsob publikování Open access Institucionální podpora MBU-M - RVO:61388971 ; BTO-N - RVO:86652036 UT WOS 000699390100001 EID SCOPUS 85114793102 DOI 10.3390/catal11091106 Anotace The natural diastereomeric mixture of silybins A and B is often used (and considered) as a single flavonolignan isolated from the fruit extract of milk thistle (Silybum marianum), silymarin. However, optically pure silybin diastereomers are required for the evaluation of their biological activity. The separation of silybin diastereomers by standard chromatographic methods is not trivial. Preparative chemoenzymatic resolution of silybin diastereomers has been published, but its optimization and scale-up are needed. Here we present a continuous flow reactor for the chemoenzymatic kinetic resolution of silybin diastereomers catalyzed by Candida antarctica lipase B (CALB) immobilized on acrylic resin beads (Novozym® 435). Temperature, flow rate, and starting material concentration were varied to determine optimal reaction conditions. The variables observed were conversion and diastereomeric ratio. Optimal conditions were chosen to allow kilogram-scale reactions and were determined to be −5 °C, 8 g/L silybin, and a flow rate of 16 mL/min. No significant carrier degradation was observed after approximately 30 cycles (30 days). Under optimal conditions and using a 1000 × 15 mm column, 20 g of silybin per day can be easily processed, yielding 6.7 and 5.6 g of silybin A and silybin B, respectively. Further scale-up depends only on the size of the reactor. Pracoviště Mikrobiologický ústav Kontakt Eliška Spurná, eliska.spurna@biomed.cas.cz, Tel.: 241 062 231 Rok sběru 2022 Elektronická adresa https://www.mdpi.com/2073-4344/11/9/1106
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