One-pot biocatalytic upgrading of lignin-derived phenol and catechol to hydroxytyrosol

Zhao, Rui-Yan; Huang, Shuang-Ping; Gao, Li-Li; Zhang, Jian-Dong

doi:10.1039/d4gc01137f

Cited by 2 publications

(1 citation statement)

References 72 publications

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“…Besides, microbial fermentation is also a promising way to produce HT from inexpensive materials. , However, the growth stage of the bacterial strain is not suitable for synthesis of HT because of its extensive antimicrobial activity. , Producing high-value-added HT from low-cost substrates is undoubtedly more competitive. Recently, a one-pot cascade biocatalytic approach for converting lignin-derived catechol and phenol into HT was reported, offering new and viable routes for the sustainable and environmentally friendly production of HT from low-cost sources . 3,4-Dihydroxybenzaldehyde, known as protocatechuic aldehyde, is a common and important building ingredient in the manufacture of antibacterial and anti-inflammatory medicines .…”

Section: Introductionmentioning

confidence: 99%

Multienzymatic Cascade for Synthesis of Hydroxytyrosol via Two-Stage Biocatalysis

Liu,

Su,

et al. 2024

J. Agric. Food Chem.

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Hydroxytyrosol, a naturally occurring compound with antioxidant and antiviral activity, is widely applied in the cosmetic, food, and nutraceutical industries. The development of a biocatalytic approach for producing hydroxytyrosol from simple and readily accessible substrates remains a challenge. Here, we designed and implemented an effective biocatalytic cascade to obtain hydroxytyrosol from 3,4-dihydroxybenzaldehyde and L-threonine via a four-step enzymatic cascade composed of seven enzymes. To prevent cross-reactions and protein expression burden caused by multiple enzymes expressed in a single cell, the designed enzymatic cascade was divided into two modules and catalyzed in a stepwise manner. The first module (FM) assisted the assembly of 3,4dihydroxybenzaldehyde and L-threonine into (2S,3R)-2-amino-3-(3,4-dihydroxyphenyl)-3-hydroxypropanoic acid, and the second module (SM) entailed converting (2S,3R)-2-amino-3-(3,4-dihydroxyphenyl)-3-hydroxypropanoic acid into hydroxytyrosol. Each module was cloned into Escherichia coli BL21 (DE3) and engineered in parallel by fine-tuning enzyme expression, resulting in two engineered whole-cell catalyst modules, BL21(FM01) and BL21(SM13), capable of converting 30 mM 3,4-dihydroxybenzaldehyde to 28.7 mM hydroxytyrosol with a high space−time yield (0.88 g/L/h). To summarize, the current study proposes a simple and effective approach for biosynthesizing hydroxytyrosol from low-cost substrates and thus has great potential for industrial applications.

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Section: Introductionmentioning

confidence: 99%

Multienzymatic Cascade for Synthesis of Hydroxytyrosol via Two-Stage Biocatalysis

Liu,

Su,

et al. 2024

J. Agric. Food Chem.

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Biocatalytic Formal Asymmetric para-Aminoethylation of Unprotected Phenols to Chiral Amines

Zhang,

Deng,

Han

et al. 2024

ACS Catal.

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Enantiomerically pure amines are vital for the development of biologically active compounds in medicine and agriculture. While aminoalkylation of phenols is well-established for creating nitrogen-containing frameworks, the regio-and stereoselective paraaminoethylation of unprotected phenols is underexplored. To fill this gap, we propose a one-pot cascade biocatalysis system for the asymmetric para-aminoethylation of unprotected phenols into chiral amines, using simple pyruvate, NH 4 Cl, and D/L-alanine as starting materials. Utilizing a modular cascade approach, we successfully performed asymmetric paraaminoethylation of unprotected phenols through a sequential process of vinylation and hydroamination, achieving good conversions (51.0−72.0%) and >99% ee for both enantiomers of amines. Additionally, biobased p-hydroxycinnamic acid and L-tyrosine and their derivatives were converted into chiral amines with moderate to good conversions (39.4−87%) and >99% ee through integrating decarboxylation/hydroamination and deamination-decarboxylation/hydroamination. This cascade marks a successful de novo biosynthesis method for the formal asymmetric para-aminoethylation of unprotected phenols.

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One-pot biocatalytic upgrading of lignin-derived phenol and catechol to hydroxytyrosol

Abstract: Upgrading lignin-derived monomeric products presents a compelling prospect for synthesizing value-added products. Despite the potential benefits, the conversion of lignin-derived phenols into hydroxytyrosol (HT), a potent natural antioxidant predominantly sourced...

Cited by 2 publications

References 72 publications

Multienzymatic Cascade for Synthesis of Hydroxytyrosol via Two-Stage Biocatalysis

Multienzymatic Cascade for Synthesis of Hydroxytyrosol via Two-Stage Biocatalysis

Biocatalytic Formal Asymmetric para-Aminoethylation of Unprotected Phenols to Chiral Amines

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