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Synthesis of long-chain alkyl glucosides via reverse hydrolysis reactions catalyzed by an engineered ß-glucosidase.
Thenchartanan, Pornpanna; Pitchayatanakorn, Phiraya; Wattana-Amorn, Pakorn; Ardá, Ana; Svasti, Jisnuson; Jiménez-Barbero, Jesús; Kongsaeree, Prachumporn T.
Afiliación
  • Thenchartanan P; Department of Biochemistry, Faculty of Science, and Center for Advanced Studies in Tropical Natural Resources, NRU-KU, Kasetsart University, Bangkok 10900, Thailand.
  • Pitchayatanakorn P; Department of Biochemistry, Faculty of Science, and Center for Advanced Studies in Tropical Natural Resources, NRU-KU, Kasetsart University, Bangkok 10900, Thailand.
  • Wattana-Amorn P; Department of Chemistry, Special Research Unit for Advanced Magnetic Resonance and Center of Excellence for Innovation in Chemistry, Faculty of Science, Kasetsart University, Bangkok 10900, Thailand.
  • Ardá A; CIC bioGUNE (Center for Cooperative Research in Biosciences); Basque Research and Technology Alliance (BRTA), Bizkaia Science and Technology Park, Bizkaia 48160, Spain.
  • Svasti J; Laboratory of Biochemistry, Chulabhorn Research Institute, Bangkok 10210, Thailand.
  • Jiménez-Barbero J; CIC bioGUNE (Center for Cooperative Research in Biosciences); Basque Research and Technology Alliance (BRTA), Bizkaia Science and Technology Park, Bizkaia 48160, Spain; Department of Organic Chemistry II, Faculty of Science & Technology, University of the Basque Country, Leioa, Bizkaia 48940, Sp
  • Kongsaeree PT; Department of Biochemistry, Faculty of Science, and Center for Advanced Studies in Tropical Natural Resources, NRU-KU, Kasetsart University, Bangkok 10900, Thailand. Electronic address: fscippt@ku.ac.th.
Enzyme Microb Technol ; 140: 109591, 2020 Oct.
Article en En | MEDLINE | ID: mdl-32912700
Long-chain alkyl glucosides, such as octyl and decyl ß-d-glucopyranosides (OG and DG, respectively), are regarded as a new generation of biodegradable, non-ionic surfactants. Previously, the mutants of Dalbergia cochinchinensis Pierre dalcochinase showed potential in the synthesis of oligosaccharides and alkyl glucosides. In this study, the N189F dalcochinase mutant gave the highest yields of OG and DG synthesis under reverse hydrolysis conditions. The optimized yield of OG (57.5 mol%) was obtained in the reactions containing 0.25 M glucose and 0.3 units of the N189 F mutant in buffer-saturated octanol at 30 °C. The identity of OG and DG products was confirmed by high resolution mass spectrometry (HRMS) and NMR. Consistent with its capability for synthesis, the reactivation kinetics and ITC analysis revealed that the aglycone binding pocket of the N189F mutant was more favorable for long-chain alkyl alcohols than the wild-type dalcochinase, while their glycone binding pockets showed similar affinity for the glucosyl moiety. STD NMR revealed higher interactions at the aglycone sites than the glycone sites. Our results demonstrated a promising potential of the N189F dalcochinase mutant in the future commercial production of long-chain alkyl glucosides via reverse hydrolysis reactions.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Beta-Glucosidasa / Glucósidos Idioma: En Revista: Enzyme Microb Technol Año: 2020 Tipo del documento: Article País de afiliación: Tailandia Pais de publicación: Estados Unidos
Texto completo
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Imprimir
XML
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Beta-Glucosidasa / Glucósidos Idioma: En Revista: Enzyme Microb Technol Año: 2020 Tipo del documento: Article País de afiliación: Tailandia Pais de publicación: Estados Unidos