Regioselective esterase-catalyzed feruloylation of l-arabinobiose

Vafiadi, Christina; Christakopoulos, Paul

doi:10.1016/j.carres.2006.05.022

Cited by 33 publications

(18 citation statements)

References 36 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Furthermore, AFA has been synthesized in detergentless microemulsions by the SF1 type C TsFaeC from Talaromyces stipitatus in low yields (21.2% after optimization of reaction conditions [3,23] and StFaeC (acetyl xylan-related enzyme; possibly SF5) from Sporotrichum thermophile (syn. M. thermophila) (up to 45% after optimization of reaction conditions) [24] coming in agreement with our observations. …”

Section: Synthesis Of L-arabinose Ferulatesupporting

confidence: 82%

The Synthetic Potential of Fungal Feruloyl Esterases: A Correlation with Current Classification Systems and Predicted Structural Properties

et al. 2018

Self Cite

View full text Add to dashboard Cite

Twenty-eight fungal feruloyl esterases (FAEs) were evaluated for their synthetic abilities in a ternary system of n-hexane: t-butanol: 100 mM MOPS-NaOH pH 6.0 forming detergentless microemulsions. Five main derivatives were synthesized, namely prenyl ferulate, prenyl caffeate, butyl ferulate, glyceryl ferulate, and L-arabinose ferulate, offering, in general, higher yields when more hydrophilic alcohol substitutions were used. Acetyl xylan esterase-related FAEs belonging to phylogenetic subfamilies (SF) 5 and 6 showed increased synthetic yields among tested enzymes. In particular, it was shown that FAEs belonging to SF6 generally transesterified aliphatic alcohols more efficiently while SF5 members preferred bulkier L-arabinose. Predicted surface properties and structural characteristics were correlated with the synthetic potential of selected tannase-related, acetyl-xylan-related, and lipase-related FAEs (SF1-2, -6, -7 members) based on homology modeling and small molecular docking simulations.

show abstract

Section: Synthesis Of L-arabinose Ferulatesupporting

confidence: 82%

The Synthetic Potential of Fungal Feruloyl Esterases: A Correlation with Current Classification Systems and Predicted Structural Properties

et al. 2018

Self Cite

View full text Add to dashboard Cite

show abstract

“…However, the fragment at m/z 409 is predicted to be formed after ring cleavage of the oligosaccharide having ferulic acid esterified on the O-2 or O-3 position of the non-reducing L-arabinofuranose ring, exhibiting signal intensity higher than the signal of the O-5 fragment at m/z 463. To the best of the author's knowledge, the enzymatic esterification of the secondary alcohol group of sugars is not possible due to steric hindrance [5,6], therefore this esterified product is hardly or not at all present in the reaction medium.…”

Section: Esi-ms N Analysis Of Feruloylated Productsmentioning

confidence: 99%

“…Various hydroxycinnamic acids (ferulic, p-coumaric, caffeic, sinapic) have widespread industrial potential by virtue of their antioxidant and antimicrobial properties [2,3]. Apart from their use as model substrates for characterisation of FAEs', methyl esters of hydroxycinnamic acids have been recently used as acid donors in transesterification reactions with aliphatic alcohols and carbohydrates [4][5][6][7].…”

Section: Introductionmentioning

confidence: 99%

“…FAEs have been used in the synthesis of sugar ferulates such as 5-O-(trans-feruloyl)-L-arabinofuranose [5] [6]. More specifically, StFaeC catalyzed the transfer of the feruloyl group to L-arabinose and L-arabinobiose in a ternary water-organic mixture consisting of n-hexane, t-butanol and water, with about 40% and 20% conversion of sugar to the feruloylated derivative, respectively [7,6].…”

Section: Introductionmentioning

confidence: 99%

“…More specifically, StFaeC catalyzed the transfer of the feruloyl group to L-arabinose and L-arabinobiose in a ternary water-organic mixture consisting of n-hexane, t-butanol and water, with about 40% and 20% conversion of sugar to the feruloylated derivative, respectively [7,6]. Commercial enzyme preparations from Humicola insolens, Thermomyces lanuginosus and Aspergillus niger exhibiting FAE activity were also used for the esterification of various glycosides at their primary hydroxyl group [8].…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Structural Characterisation by ESI-MS of Feruloylated Arabino-oligosaccharides Synthesised by Chemoenzymatic Esterification

et al. 2007

Self Cite

View full text Add to dashboard Cite

show abstract

Heterologous production of a feruloyl esterase from Pleurotus sapidus synthesizing feruloyl‐saccharide esters

Kelle

Nieter

Krings

et al. 2015

Biotech and App Biochem

View full text Add to dashboard Cite

The feruloyl esterase (FAE) gene EST1 from the basidiomycete Pleurotus sapidus was heterologously expressed in Escherichia coli and Pichia pastoris. Catalytically active recombinant Est1 was secreted using P. pastoris as a host. For expression in P. pastoris, the expression vector pPIC9K was applied. The EST1 gene was cloned with an N-terminal α-mating factor pre-pro sequence and expressed under the control of a methanol inducible alcohol oxidase 1 promotor. Est1 was purified to homogeneity using ion exchange and hydrophobic interaction chromatography. The recombinant Est1 showed optima at pH 5.0 and 50 °C, and released ferulic acid from saccharide esters and from the natural substrate destarched wheat bran. Substrate specificity profile and descriptor-based analysis demonstrated unique properties, showing that Est1 did not fit into the current FAE classification model. Transferuloylation synthesis of feruloyl-saccharide esters was proven for mono- and disaccharides.

show abstract

Regioselective esterase-catalyzed feruloylation of l-arabinobiose

Cited by 33 publications

References 36 publications

The Synthetic Potential of Fungal Feruloyl Esterases: A Correlation with Current Classification Systems and Predicted Structural Properties

The Synthetic Potential of Fungal Feruloyl Esterases: A Correlation with Current Classification Systems and Predicted Structural Properties

Structural Characterisation by ESI-MS of Feruloylated Arabino-oligosaccharides Synthesised by Chemoenzymatic Esterification

Heterologous production of a feruloyl esterase from Pleurotus sapidus synthesizing feruloyl‐saccharide esters

Contact Info

Product

Resources

About