Facile enzymatic Cγ-acylation of lignin model compounds

Roelant Hilgers, Jean Paul Vincken, Mirjam A. Kabel*

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

Abstract

Simple β-O-4’ linked dimeric model compounds are often targeted as substrate to mimic the reactivity of lignin in enzymatic or chemical treatments. These models mimic the structure and reactivity of regular β-O-4′ linkages in lignin, but are less suitable to predict the reactivity of acylated β-O-4′ substructures, which are abundant in various types of lignin. Here, we present a one-step lipase-catalyzed acylation of a commercially available lignin model compound with p-coumaric acid, p-hydroxybenzoic acid, cinnamic acid and acetic acid as acyl donors. This facile procedure allows to obtain new and relevant lignin model compounds at milligram scale, with simple purification of products and unreacted substrate.

Original languageEnglish
Article number105919
JournalCatalysis Communications
Volume136
DOIs
Publication statusPublished - 1 Mar 2020

Fingerprint

Acylation
Lignin
Acids
Hydroxybenzoates
Lipases
Substrates
Lipase
Acetic acid
Acetic Acid
Purification

Keywords

  • CALB
  • Esterification
  • Lipase
  • p-coumaric acid
  • p-hydroxybenzoic acid
  • Synthesis

Cite this

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title = "Facile enzymatic Cγ-acylation of lignin model compounds",
abstract = "Simple β-O-4’ linked dimeric model compounds are often targeted as substrate to mimic the reactivity of lignin in enzymatic or chemical treatments. These models mimic the structure and reactivity of regular β-O-4′ linkages in lignin, but are less suitable to predict the reactivity of acylated β-O-4′ substructures, which are abundant in various types of lignin. Here, we present a one-step lipase-catalyzed acylation of a commercially available lignin model compound with p-coumaric acid, p-hydroxybenzoic acid, cinnamic acid and acetic acid as acyl donors. This facile procedure allows to obtain new and relevant lignin model compounds at milligram scale, with simple purification of products and unreacted substrate.",
keywords = "CALB, Esterification, Lipase, p-coumaric acid, p-hydroxybenzoic acid, Synthesis",
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Facile enzymatic Cγ-acylation of lignin model compounds. / Hilgers, Roelant; Vincken, Jean Paul; Kabel, Mirjam A.

In: Catalysis Communications, Vol. 136, 105919, 01.03.2020.

Research output: Contribution to journalArticleAcademicpeer-review

TY - JOUR

T1 - Facile enzymatic Cγ-acylation of lignin model compounds

AU - Hilgers, Roelant

AU - Vincken, Jean Paul

AU - Kabel, Mirjam A.

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Y1 - 2020/3/1

N2 - Simple β-O-4’ linked dimeric model compounds are often targeted as substrate to mimic the reactivity of lignin in enzymatic or chemical treatments. These models mimic the structure and reactivity of regular β-O-4′ linkages in lignin, but are less suitable to predict the reactivity of acylated β-O-4′ substructures, which are abundant in various types of lignin. Here, we present a one-step lipase-catalyzed acylation of a commercially available lignin model compound with p-coumaric acid, p-hydroxybenzoic acid, cinnamic acid and acetic acid as acyl donors. This facile procedure allows to obtain new and relevant lignin model compounds at milligram scale, with simple purification of products and unreacted substrate.

AB - Simple β-O-4’ linked dimeric model compounds are often targeted as substrate to mimic the reactivity of lignin in enzymatic or chemical treatments. These models mimic the structure and reactivity of regular β-O-4′ linkages in lignin, but are less suitable to predict the reactivity of acylated β-O-4′ substructures, which are abundant in various types of lignin. Here, we present a one-step lipase-catalyzed acylation of a commercially available lignin model compound with p-coumaric acid, p-hydroxybenzoic acid, cinnamic acid and acetic acid as acyl donors. This facile procedure allows to obtain new and relevant lignin model compounds at milligram scale, with simple purification of products and unreacted substrate.

KW - CALB

KW - Esterification

KW - Lipase

KW - p-coumaric acid

KW - p-hydroxybenzoic acid

KW - Synthesis

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M3 - Article

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JO - Catalysis Communications

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