Production and Surfactant Properties of Tert-Butyl α-d-Glucopyranosides Catalyzed by Cyclodextrin Glucanotransferase
| Autor: | Francisco J. Plou, Manuel Bernabé, Jose L. Gonzalez-Alfonso, Antonio Ballesteros, Humberto García-Arellano, José-Luis Parra, Miguel Alcalde, Francesc Comelles, Claudia Ubilla |
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| Přispěvatelé: | Ministerio de Economía y Competitividad (España), European Cooperation in Science and Technology, CSIC - Unidad de Recursos de Información Científica para la Investigación (URICI), Ministerio de Educación (España) |
| Jazyk: | angličtina |
| Rok vydání: | 2019 |
| Předmět: |
Transglycosylation
Glycosylation biocatalysis Starch glycosidases Alcohol macromolecular substances lcsh:Chemical technology 01 natural sciences Medicinal chemistry Catalysis lcsh:Chemistry 03 medical and health sciences chemistry.chemical_compound Hydrolysis biosurfactants Pulmonary surfactant alkyl glucosides lcsh:TP1-1185 Physical and Theoretical Chemistry Glycosidases 030304 developmental biology chemistry.chemical_classification 0303 health sciences Cyclodextrin cyclodextrin glycosyltransferases 010405 organic chemistry 0104 chemical sciences carbohydrates (lipids) Alkyl glucosides chemistry lcsh:QD1-999 Biocatalysis Yield (chemistry) Biosurfactants lipids (amino acids peptides and proteins) Cyclodextrin glycosyltransferases transglycosylation |
| Zdroj: | Catalysts Volume 9 Issue 7 Catalysts, Vol 9, Iss 7, p 575 (2019) Digital.CSIC. Repositorio Institucional del CSIC instname |
| ISSN: | 2073-4344 |
| DOI: | 10.3390/catal9070575 |
| Popis: | While testing the ability of cyclodextrin glucanotransferases (CGTases) to glucosylate a series of flavonoids in the presence of organic cosolvents, we found out that this enzyme was able to glycosylate a tertiary alcohol (tert-butyl alcohol). In particular, CGTases from Thermoanaerobacter sp. and Thermoanaerobacterium thermosulfurigenes EM1 gave rise to the appearance of at least two glycosylation products, which were characterized by mass spectrometry (MS) and nuclear magnetic resonance (NMR) as tert-butyl-&alpha D-glucoside (major product) and tert-butyl-&alpha D-maltoside (minor product). Using partially hydrolyzed starch as glucose donor, the yield of transglucosylation was approximately 44% (13 g/L of tert-butyl-&alpha D-glucoside and 4 g/L of tert-butyl-&alpha D-maltoside). The synthesized tert-butyl-&alpha D-glucoside exhibited the typical surfactant behavior (critical micellar concentration, 4.0&ndash 4.5 mM) and its properties compared well with those of the related octyl-&alpha D-glucoside. To the best of our knowledge, this is the first description of an enzymatic &alpha glucosylation of a tertiary alcohol. |
| Databáze: | OpenAIRE |
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