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Production and Surfactant Properties of Tert-Butyl α-d-Glucopyranosides Catalyzed by Cyclodextrin Glucanotransferase

1
Instituto de Catálisis y Petroleoquímica, CSIC, 28049 Madrid, Spain
2
Departamento de Ciencias Ambientales, División de Ciencias Biológicas y de la Salud, Universidad Autónoma Metropolitana, Unidad Lerma, Av. de las Garzas 10, Lerma de Villada, Estado de México 52006, Mexico
3
Escuela de Ingeniería Bioquímica, Pontificia Universidad Católica de Valparaíso, Valparaíso 2147, Chile
4
Instituto de Investigaciones Químicas y Ambientales, CSIC, 08034 Barcelona, Spain
5
Instituto de Química Orgánica, CSIC, 28006 Madrid, Spain
*
Author to whom correspondence should be addressed.
Dedicated to the memory of Prof. Manuel Bernabé, deceased on April 2018.
Catalysts 2019, 9(7), 575; https://doi.org/10.3390/catal9070575
Received: 28 May 2019 / Revised: 20 June 2019 / Accepted: 26 June 2019 / Published: 29 June 2019
(This article belongs to the Special Issue Biocatalysis: Chemical Biosynthesis)
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Abstract

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-α-D-glucoside (major product) and tert-butyl-α-D-maltoside (minor product). Using partially hydrolyzed starch as glucose donor, the yield of transglucosylation was approximately 44% (13 g/L of tert-butyl-α-D-glucoside and 4 g/L of tert-butyl-α-D-maltoside). The synthesized tert-butyl-α-D-glucoside exhibited the typical surfactant behavior (critical micellar concentration, 4.0–4.5 mM) and its properties compared well with those of the related octyl-α-D-glucoside. To the best of our knowledge, this is the first description of an enzymatic α-glucosylation of a tertiary alcohol. View Full-Text
Keywords: biocatalysis; glycosidases; transglycosylation; cyclodextrin glycosyltransferases; alkyl glucosides; biosurfactants biocatalysis; glycosidases; transglycosylation; cyclodextrin glycosyltransferases; alkyl glucosides; biosurfactants
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Garcia-Arellano, H.; Gonzalez-Alfonso, J.L.; Ubilla, C.; Comelles, F.; Alcalde, M.; Bernabé, M.; Parra, J.-L.; Ballesteros, A.O.; Plou, F.J. Production and Surfactant Properties of Tert-Butyl α-d-Glucopyranosides Catalyzed by Cyclodextrin Glucanotransferase. Catalysts 2019, 9, 575.

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