The synthetic potential of fungal feruloyl esterases: A correlation with current classification systems and predicted structural properties

Io Antonopoulou; Adiphol Dilokpimol; Laura Iancu; Miia R. Mäkelä; Simona Varriale; Gabriella Cerullo; Silvia Hüttner; Stefan Uthoff; Peter Jütten; Alexander Piechot; Alexander Steinbüchel; Lisbeth Olsson; Vincenza Faraco; Kristiina S. Hildén; Ronald P. de Vries; Ulrika Rova; Paul Christakopoulos

doi:10.3390/catal8060242

The synthetic potential of fungal feruloyl esterases: A correlation with current classification systems and predicted structural properties

Io Antonopoulou
, Adiphol Dilokpimol
, Laura Iancu
, Miia R. Mäkelä
, Simona Varriale
, Gabriella Cerullo
, Silvia Hüttner
, Stefan Uthoff
, Peter Jütten
, Alexander Piechot
, Alexander Steinbüchel
, Lisbeth Olsson
, Vincenza Faraco
, Kristiina S. Hildén
, Ronald P. de Vries
, Ulrika Rova
, Paul Christakopoulos^*

^*Corresponding author for this work

Not published at VTT

Luleå University of Technology
Utrecht University
DuPont
University of Helsinki
University of Naples Federico II
Chalmers University of Technology
University of Münster
Taros Chemicals GmbH & Co KG
King Abdulaziz University

Research output: Contribution to journal › Article › Scientific › peer-review

15 Citations (Scopus)

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.

Original language	English
Article number	242
Journal	Catalysts
Volume	8
Issue number	6
DOIs	https://doi.org/10.3390/catal8060242
Publication status	Published - 7 Jun 2018
MoE publication type	A1 Journal article-refereed

Funding

This work was supported by the European Union, grant agreement no: 613868 (OPTIBIOCAT).

Keywords

Antioxidants
Butyl ferulate
Feruloyl esterase
Glyceryl ferulate
L-arabinose ferulate
Phylogenetic classification
Prenyl caffeate
Prenyl ferulate
Sugar esters
Transesterification

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10.3390/catal8060242

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Antonopoulou, I., Dilokpimol, A., Iancu, L., Mäkelä, M. R., Varriale, S., Cerullo, G., Hüttner, S., Uthoff, S., Jütten, P., Piechot, A., Steinbüchel, A., Olsson, L., Faraco, V., Hildén, K. S., de Vries, R. P., Rova, U., & Christakopoulos, P. (2018). The synthetic potential of fungal feruloyl esterases: A correlation with current classification systems and predicted structural properties. Catalysts, 8(6), Article 242. https://doi.org/10.3390/catal8060242

@article{9aa8acacc7724497807bc0e6ec7cb7b6,

title = "The synthetic potential of fungal feruloyl esterases: A correlation with current classification systems and predicted structural properties",

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.",

keywords = "Antioxidants, Butyl ferulate, Feruloyl esterase, Glyceryl ferulate, L-arabinose ferulate, Phylogenetic classification, Prenyl caffeate, Prenyl ferulate, Sugar esters, Transesterification",

author = "Io Antonopoulou and Adiphol Dilokpimol and Laura Iancu and M{\"a}kel{\"a}, \{Miia R.\} and Simona Varriale and Gabriella Cerullo and Silvia H{\"u}ttner and Stefan Uthoff and Peter J{\"u}tten and Alexander Piechot and Alexander Steinb{\"u}chel and Lisbeth Olsson and Vincenza Faraco and Hild{\'e}n, \{Kristiina S.\} and \{de Vries\}, \{Ronald P.\} and Ulrika Rova and Paul Christakopoulos",

note = "Funding Information: This work was supported by the European Union, grant agreement no: 613868 (OPTIBIOCAT). Funding Information: Biochemical Process Engineering, Division of Chemical Engineering, Department of Civil, Environmental and Natural Resources Engineering, Lule{\aa} University of Technology, SE-97187 Lule{\aa}, Sweden; [email protected] (I.A.); [email protected] (U.R.) Fungal Physiology, Westerdijk Fungal Biodiversity Institute \& Fungal Molecular Physiology, Utrecht University, Uppsalalaan 8, 3584 CT Utrecht, The Netherlands; [email protected] (A.D.); [email protected] (R.P.d.V.) Dupont Industrial Biosciences, Nieuwe Kanaal 7-S, 6709 PA Wageningen, The Netherlands; [email protected] Department of Microbiology, University of Helsinki, Viikinkaari 9, 00014-FIN Helsinki, Finland; [email protected] (M.R.M.); [email protected] (K.S.H.) Department of Chemical Sciences, University of Naples “Federico II”, Complesso Universitario Monte S. Angelo Via Cintia, 4 IT-80126 Naples, Italy; [email protected] (S.V.); [email protected] (G.C.); [email protected] (V.F.) Department of Biology and Biological Engineering, Division of Industrial Biotechnology, Chalmers University of Technology, SE-41296 Gothenburg, Sweden; [email protected] (S.H.); [email protected] (L.O.) Institut f{\"u}r Molekulare Mikrobiologie und Biotechnologie, Westf{\"a}lische Wilhelms-Universit{\"a}t M{\"u}nster, Corrensstra{\ss}e 3, 48149 Munich, Germany; [email protected] (S.U.); [email protected] (A.S.) Taros Chemicals GmbH \& Co KG, Emil-Figge-Str. 76a, 44227 Dortmund, Germany; [email protected] (P.J.); [email protected] (A.P.) Environmental Sciences Department, King Abdulaziz University, Jeddah 21589, Saudi Arabia Correspondence: [email protected]; Tel.: +46-(0)920-492510 Publisher Copyright: {\textcopyright} 2018 by the authors. Licensee MDPI, Basel, Switzerland.",

year = "2018",

month = jun,

day = "7",

doi = "10.3390/catal8060242",

language = "English",

volume = "8",

journal = "Catalysts",

issn = "2073-4344",

publisher = "MDPI",

number = "6",

}

Antonopoulou, I, Dilokpimol, A, Iancu, L, Mäkelä, MR, Varriale, S, Cerullo, G, Hüttner, S, Uthoff, S, Jütten, P, Piechot, A, Steinbüchel, A, Olsson, L, Faraco, V, Hildén, KS, de Vries, RP, Rova, U & Christakopoulos, P 2018, 'The synthetic potential of fungal feruloyl esterases: A correlation with current classification systems and predicted structural properties', Catalysts, vol. 8, no. 6, 242. https://doi.org/10.3390/catal8060242

TY - JOUR

T1 - The synthetic potential of fungal feruloyl esterases

T2 - A correlation with current classification systems and predicted structural properties

AU - Antonopoulou, Io

AU - Dilokpimol, Adiphol

AU - Iancu, Laura

AU - Mäkelä, Miia R.

AU - Varriale, Simona

AU - Cerullo, Gabriella

AU - Hüttner, Silvia

AU - Uthoff, Stefan

AU - Jütten, Peter

AU - Piechot, Alexander

AU - Steinbüchel, Alexander

AU - Olsson, Lisbeth

AU - Faraco, Vincenza

AU - Hildén, Kristiina S.

AU - de Vries, Ronald P.

AU - Rova, Ulrika

AU - Christakopoulos, Paul

N1 - Funding Information: This work was supported by the European Union, grant agreement no: 613868 (OPTIBIOCAT). Funding Information: Biochemical Process Engineering, Division of Chemical Engineering, Department of Civil, Environmental and Natural Resources Engineering, Luleå University of Technology, SE-97187 Luleå, Sweden; [email protected] (I.A.); [email protected] (U.R.) Fungal Physiology, Westerdijk Fungal Biodiversity Institute & Fungal Molecular Physiology, Utrecht University, Uppsalalaan 8, 3584 CT Utrecht, The Netherlands; [email protected] (A.D.); [email protected] (R.P.d.V.) Dupont Industrial Biosciences, Nieuwe Kanaal 7-S, 6709 PA Wageningen, The Netherlands; [email protected] Department of Microbiology, University of Helsinki, Viikinkaari 9, 00014-FIN Helsinki, Finland; [email protected] (M.R.M.); [email protected] (K.S.H.) Department of Chemical Sciences, University of Naples “Federico II”, Complesso Universitario Monte S. Angelo Via Cintia, 4 IT-80126 Naples, Italy; [email protected] (S.V.); [email protected] (G.C.); [email protected] (V.F.) Department of Biology and Biological Engineering, Division of Industrial Biotechnology, Chalmers University of Technology, SE-41296 Gothenburg, Sweden; [email protected] (S.H.); [email protected] (L.O.) Institut für Molekulare Mikrobiologie und Biotechnologie, Westfälische Wilhelms-Universität Münster, Corrensstraße 3, 48149 Munich, Germany; [email protected] (S.U.); [email protected] (A.S.) Taros Chemicals GmbH & Co KG, Emil-Figge-Str. 76a, 44227 Dortmund, Germany; [email protected] (P.J.); [email protected] (A.P.) Environmental Sciences Department, King Abdulaziz University, Jeddah 21589, Saudi Arabia Correspondence: [email protected]; Tel.: +46-(0)920-492510 Publisher Copyright: © 2018 by the authors. Licensee MDPI, Basel, Switzerland.

PY - 2018/6/7

Y1 - 2018/6/7

N2 - 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.

AB - 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.

KW - Antioxidants

KW - Butyl ferulate

KW - Feruloyl esterase

KW - Glyceryl ferulate

KW - L-arabinose ferulate

KW - Phylogenetic classification

KW - Prenyl caffeate

KW - Prenyl ferulate

KW - Sugar esters

KW - Transesterification

UR - https://www.scopus.com/pages/publications/85049258432

U2 - 10.3390/catal8060242

DO - 10.3390/catal8060242

M3 - Article

AN - SCOPUS:85049258432

SN - 2073-4344

VL - 8

JO - Catalysts

JF - Catalysts

IS - 6

M1 - 242

ER -

The synthetic potential of fungal feruloyl esterases: A correlation with current classification systems and predicted structural properties

Abstract

Funding

Keywords

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