Bioreductions catalyzed by an alcohol dehydrogenase in non-aqueous media

verfasst von: Selin Kara, Dominik Spickermann, Andrea Weckbecker, Christian Leggewie, Isabel W.C.E. Arends, Frank Hollmann
Abstract: Highly productive biocatalytic reductions were established using an isolated alcohol dehydrogenase (ADH) under water-deficient conditions. First, a solvent-free system was evaluated for the reduction of 2-butanone catalyzed by ADH evo-1.1.200 promoted by the "smart cosubstrate" 1,4-butanediol. ADH evo-1.1.200 excelled by its activity and stability under high reagent concentrations and hence was the enzyme of choice. However, conversion of 2-butanone was limited to <1 % in 10 days under the solvent-free conditions. Therefore, water-immiscible organic solvents were evaluated whereby the highest conversions were achieved in MTBE and toluene. MTBE was chosen as its different boiling point compared to other reaction components (e.g., 2-butanone, 2-butanol, diol cosubstrate, and lactone coproduct) would simplify the downstream processing. Further on, by tuning substrate loading, the productivity of the ADH evo-1.1.200 was successfully increased to a turnover number (TON) of 64 000. Practical water-deficient enzymology for bioreductions: The use of alcohol dehydrogenases (ADHs) in neat substrates and in water-immiscible organic solvents is explored. The ADH evo-1.1.200 excelled by its high stability, as it showed significant catalytic activity over days. Reductions are coupled with the "smart cosubstrate" 1,4-butanediol; hence, excess amounts of reductants are avoided.
Externe Organisation(en): Technische Universität Dresden (TUD)
Delft University of Technology
evoxx technologies GmbH
Typ: Artikel
Journal: CHEMCATCHEM
Band: 6
Seiten: 973-976
Anzahl der Seiten: 4
ISSN: 1867-3880
Publikationsdatum: 10.04.2014
Publikationsstatus: Veröffentlicht
Peer-reviewed: Ja
ASJC Scopus Sachgebiete: Katalyse, Physikalische und Theoretische Chemie, Organische Chemie, Anorganische Chemie
Elektronische Version(en): https://doi.org/10.1002/cctc.201300841 (Zugang: Geschlossen)

BibTeX

@article{b115deead436496cbc840d1546ad806d,
title = "Bioreductions catalyzed by an alcohol dehydrogenase in non-aqueous media",
abstract = "Highly productive biocatalytic reductions were established using an isolated alcohol dehydrogenase (ADH) under water-deficient conditions. First, a solvent-free system was evaluated for the reduction of 2-butanone catalyzed by ADH evo-1.1.200 promoted by the {"}smart cosubstrate{"} 1,4-butanediol. ADH evo-1.1.200 excelled by its activity and stability under high reagent concentrations and hence was the enzyme of choice. However, conversion of 2-butanone was limited to <1 % in 10 days under the solvent-free conditions. Therefore, water-immiscible organic solvents were evaluated whereby the highest conversions were achieved in MTBE and toluene. MTBE was chosen as its different boiling point compared to other reaction components (e.g., 2-butanone, 2-butanol, diol cosubstrate, and lactone coproduct) would simplify the downstream processing. Further on, by tuning substrate loading, the productivity of the ADH evo-1.1.200 was successfully increased to a turnover number (TON) of 64 000. Practical water-deficient enzymology for bioreductions: The use of alcohol dehydrogenases (ADHs) in neat substrates and in water-immiscible organic solvents is explored. The ADH evo-1.1.200 excelled by its high stability, as it showed significant catalytic activity over days. Reductions are coupled with the {"}smart cosubstrate{"} 1,4-butanediol; hence, excess amounts of reductants are avoided.",
keywords = "alcohol dehydrogenases, biotransformations, organic media, reduction, smart cosubstrates",
author = "Selin Kara and Dominik Spickermann and Andrea Weckbecker and Christian Leggewie and Arends, {Isabel W.C.E.} and Frank Hollmann",
year = "2014",
month = apr,
day = "10",
doi = "10.1002/cctc.201300841",
language = "English",
volume = "6",
pages = "973--976",
journal = "CHEMCATCHEM",
issn = "1867-3880",
publisher = "Wiley - VCH Verlag GmbH & CO. KGaA",
number = "4",
}