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. Makela; Simona Varriale; Gabriella Cerullo; Silvia Huttner; Stefan Uthoff; Peter Juetten; Alexander Piechot; Alexander Steinbuechel; Lisbeth Olsson; Vincenza Faraco; Kristiina S. Hilden; 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. Makela, Simona Varriale, Gabriella Cerullo, Silvia Huttner, Stefan Uthoff, Peter Juetten, Alexander Piechot, Alexander Steinbuechel, Lisbeth Olsson, Vincenza Faraco, Kristiina S. Hilden, Ronald P. de Vries, Ulrika Rova, Paul Christakopoulos

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

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
Number of pages	22
Journal	Catalysts
Volume	8
Issue number	6
DOIs	https://doi.org/10.3390/catal8060242
Publication status	Published - Jun 2018

Keywords

transesterification
feruloyl esterase
antioxidants
phylogenetic classification
prenyl ferulate
prenyl caffeate
glyceryl ferulate
butyl ferulate
L-arabinose ferulate
sugar esters

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Antonopoulou, I., Dilokpimol, A., Iancu, L., Makela, M. R., Varriale, S., Cerullo, G., Huttner, S., Uthoff, S., Juetten, P., Piechot, A., Steinbuechel, A., Olsson, L., Faraco, V., Hilden, 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

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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 = "transesterification, feruloyl esterase, antioxidants, phylogenetic classification, prenyl ferulate, prenyl caffeate, glyceryl ferulate, butyl ferulate, L-arabinose ferulate, sugar esters",

author = "Io Antonopoulou and Adiphol Dilokpimol and Laura Iancu and Makela, {Miia R.} and Simona Varriale and Gabriella Cerullo and Silvia Huttner and Stefan Uthoff and Peter Juetten and Alexander Piechot and Alexander Steinbuechel and Lisbeth Olsson and Vincenza Faraco and Hilden, {Kristiina S.} and {de Vries}, {Ronald P.} and Ulrika Rova and Paul Christakopoulos",

year = "2018",

month = jun,

doi = "10.3390/catal8060242",

language = "English",

volume = "8",

journal = "Catalysts",

issn = "2073-4344",

publisher = "Multidisciplinary Digital Publishing Institute",

number = "6",

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Antonopoulou, I, Dilokpimol, A, Iancu, L, Makela, MR, Varriale, S, Cerullo, G, Huttner, S, Uthoff, S, Juetten, P, Piechot, A, Steinbuechel, A, Olsson, L, Faraco, V, Hilden, 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 - Makela, Miia R.

AU - Varriale, Simona

AU - Cerullo, Gabriella

AU - Huttner, Silvia

AU - Uthoff, Stefan

AU - Juetten, Peter

AU - Piechot, Alexander

AU - Steinbuechel, Alexander

AU - Olsson, Lisbeth

AU - Faraco, Vincenza

AU - Hilden, Kristiina S.

AU - de Vries, Ronald P.

AU - Rova, Ulrika

AU - Christakopoulos, Paul

PY - 2018/6

Y1 - 2018/6

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 - transesterification

KW - feruloyl esterase

KW - antioxidants

KW - phylogenetic classification

KW - prenyl ferulate

KW - prenyl caffeate

KW - glyceryl ferulate

KW - butyl ferulate

KW - L-arabinose ferulate

KW - sugar esters

U2 - 10.3390/catal8060242

DO - 10.3390/catal8060242

M3 - Article

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

Keywords

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