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Abstract
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.
Highlights
Feruloyl esterases (EC 3.1.1.73, feruloyl esterases (FAEs)) are a subclass of carbohydrate esterases generally known for their role as accessory enzymes during the enzymatic hydrolysis of lignocellulosic biomass, being able to break down the ester bond between hydroxycinnamic acids, such as ferulic acid (FA), sinapic acid (SA), caffeic acid (CA), and p-coumaric acid and sugars in plant cell walls
Screening of FAEs using different alcohol acceptors showed that higher transesterification rates, yields, and selectivities were observed for more hydrophilic/polar alcohols and, in decreasing order of preference, of glycerol >
The transesterification trend/pattern among evaluated FAEs was quite similar between different alcohol acceptors at given conditions
Summary
Feruloyl esterases (EC 3.1.1.73, FAEs) are a subclass of carbohydrate esterases generally known for their role as accessory enzymes during the enzymatic hydrolysis of lignocellulosic biomass, being able to break down the ester bond between hydroxycinnamic acids, such as ferulic acid (FA), sinapic acid (SA), caffeic acid (CA), and p-coumaric acid (pCA) and sugars in plant cell walls. Contrary to lipases, which perform best in pure solvents, the vast majority of synthetic reactions based on FAEs have been performed in ternary solvent systems forming detergentless microemulsions, since FAEs often inactivate during incubation in pure solvents with very low or no water content [13,14]. The initial classification of FAEs (type A–D) was based on their hydrolytic activities towards model substrates (methyl ferulate, MFA; methyl sinapate, MSA; methyl caffeate, MCA, and methyl p-coumarate; MpCA) and was later supported by amino acid similarity and phylogenetic analysis [19].
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