Substrate specificity in hydrolysis and transglucosylation by family 1 β-glucosidases from cassava and Thai rosewood

Kongsaeree, Prachumporn T.; Ratananikom, Khakhanang; Choengpanya, Khuanjarat; Tongtubtim, Nusra; Sujiwattanarat, Penporn; Porncharoennop, Chompoonuth; Onpium, Amornrat; Svasti, Jisnuson

doi:10.1016/j.molcatb.2010.09.003

Cited by 16 publications

(12 citation statements)

References 26 publications

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“…Jiang et al were able to synthesize tert-butyl β-D-xyloside and xylobioside with xylan as sugar donor, in the presence of 20% tert-butyl alcohol, employing a xylanase from Thermotoga maritima [48]. Kongsaree et al reported in 2010 that linamarase (a cyanogenic β-glucosidase) also catalyzed transglucosylation reactions with tertiary alcohols as acceptors and pNP-glycosides as donors [49].…”

Section: Sourcementioning

confidence: 99%

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

et al. 2019

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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.

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Section: Sourcementioning

confidence: 99%

“…[48]. Kongsaree et al reported in 2010 that linamarase (a cyanogenic β-glucosidase) also catalyzed transglucosylation reactions with tertiary alcohols as acceptors and pNP-glycosides as donors [49].…”

Section: Progress Of Tert-butyl Alcohol Glucosylation By Thermoanaeromentioning

confidence: 99%

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

et al. 2019

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“…The cultures were grown in a 1-l medium and induced under the same culture conditions as described above [20,31]. 0.5% (v/v) Methanol was added every day until the activity did not increase any further.…”

Section: Expression and Purification Of The Recombinant Anbxmentioning

confidence: 99%

“…To check the hydrolysis product, 10 ll of reaction was also spotted on TLC plate (Silica gel 60 F254), which was developed twice in ethyl acetate:methanol:water, 16:6:1 by volume. The spots were visualized by soaking in 20% sulfuric acid in ethanol, and heating on the hotplate until the spots could be observed [31].…”

Section: Hydrolysis Of Xylan By the Recombinant Anbxmentioning

confidence: 99%

Cloning, expression and characterization of β-xylosidase from Aspergillus niger ASKU28

Choengpanya

Arthornthurasuk

Wattana-Amorn

et al. 2015

Protein Expression and Purification

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“…From these complexes, one was randomly selected per target protein, and then minimized using the standard Tripos molecular mechanics (MM) force field of the SYBYL molecular modeling package, following a Powell energy minimization algorithm, applying GasteigerHückel charges and 0.005 kcal mol -1 Å -1 energy gradient convergence criterion. 37,38 Following this optimization, molecular dynamics (MD) simulations were performed in vacuo using SYBYL 8.1 force field. 39 The protocol included (i) a 5000 fs period, beginning at 0 to 300 K, as a heating protocol, (ii) a 10000 fs period at 300 K was employed for equilibration and (iii) 20000 fs at 300 K were used in the simulations with a time step of 1 fs.…”

Section: Counterpoise-corrected Interaction Energy (Cp-cie) Calculationsmentioning

confidence: 99%

Searching of protein targets for alpha lipoic acid

Maldonado-Rojas¹,

Olívero-Verbel²,

Ortega-Zúñiga³

2011

J. Braz. Chem. Soc.

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Ácido alfa lipóico (ALA) é um dos oxidantes mais poderosos e um cofactor em complexos enzimáticos, apesar de seus mecanismos ainda não serem conhecidos. A pesquisa por alvos proteicos de ALA é fundamental para compreender seus processos de sinalização. Uma abordagem bioinformática foi usada a fim de se encontrar alvos hipotéticos para ALA usando o servidor Target Fishing Dock (TarFisDock). Contagens de afinidade para os melhores resultados foram calculadas pelo AutoDock Vina. Alvos relevantes incluíram leucotrieno A4 hidrolase, canal de potássio voltagem-dependente, alfa-hidroxiesteróide desidrogenase, epóxido hidrolase, proteínas estas envolvidas no câncer, diabetes, desordens neurológica e cardiovascular. As energias de interação corrigidas segundo padrão conterpoise foram calculadas para proteínas que ligam R-ALA, e mostraram interações R-ALA-resíduos favoráveis. A sobreposição de R-ALA com inibidores conhecidos daquelas proteínas, permitu concluir que R-ALA adota diferentes conformações espaciais em seus sítios de ligação, podendo ser um inibidor fraco plausível destes alvos e, portanto, este efeito deveria ser considerado quando da realização de estudos sobre seus efeitos bioquímicos.Alpha lipoic acid (ALA) is one of the most powerful antioxidants and a cofactor in enzyme complexes, although its mechanisms are still unknown. The search for protein targets of ALA is fundamental to understand its signaling pathways. A bioinformatics approach was used to find hypothetical targets for ALA using the Target Fishing Dock Server (TarFisDock). Affinity scores for the best hits were calculated by AutoDock Vina. Relevant targets included leukotriene A4 hydrolase, voltage gated potassium channel, alpha hydroxysteroid dehydrogenase and epoxide hydrolase, proteins involved in cancer, diabetes, and neurological and cardiovascular disorders. The counterpoise-corrected interaction energies calculated for proteins that bind R-ALA showed favorable interactions R-ALA-residues. Superpositioning of R-ALA with known inhibitors of those proteins, together with the finding that R-ALA adopts different spatial conformations in their binding sites, suggests R-ALA could be a plausible weak inhibitor of these targets, and this effect should be considered when studying its biochemical effects.

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Substrate specificity in hydrolysis and transglucosylation by family 1 β-glucosidases from cassava and Thai rosewood

Cited by 16 publications

References 26 publications

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

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

Cloning, expression and characterization of β-xylosidase from Aspergillus niger ASKU28

Searching of protein targets for alpha lipoic acid

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