Methanol-Driven Oxidative Rearrangement of Biogenic Furans – Enzyme Cascades vs. Photobiocatalysis

Christina Jäger; Cloé Bruneau; Philip K. Wagner; Martin H.G. Prechtl; Jan Deska

doi:10.3389/fchem.2021.635883

Methanol-Driven Oxidative Rearrangement of Biogenic Furans – Enzyme Cascades vs. Photobiocatalysis

Christina Jäger, Cloé Bruneau, Philip K. Wagner, Martin H.G. Prechtl, Jan Deska^*

^*Corresponding author for this work

Department of Chemistry and Materials Science

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Abstract

The oxidative ring expansion of bio-derived furfuryl alcohols to densely functionalized six-membered O-heterocycles represents an attractive strategy in the growing network of valorization routes to synthetic building blocks out of the lignocellulosic biorefinery feed. In this study, two scenarios for the biocatalytic Achmatowicz-type rearrangement using methanol as terminal sacrificial reagent have been evaluated, comparing multienzymatic cascade designs with a photo-bio-coupled activation pathway.

Original language	English
Article number	635883
Number of pages	6
Journal	Frontiers in Chemistry
Volume	9
DOIs	https://doi.org/10.3389/fchem.2021.635883
Publication status	Published - 7 Apr 2021
MoE publication type	A1 Journal article-refereed

Keywords

aerobic
enzymatic
furans
oxygenation
ring expansion
visible light

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CHEM_Jager_et_al_Methanol-Driven_Oxidative_Rearrangement_2021_Frontiers_in_ChemistryFinal published version, 1.18 MBLicence: CC BY

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title = "Methanol-Driven Oxidative Rearrangement of Biogenic Furans – Enzyme Cascades vs. Photobiocatalysis",

abstract = "The oxidative ring expansion of bio-derived furfuryl alcohols to densely functionalized six-membered O-heterocycles represents an attractive strategy in the growing network of valorization routes to synthetic building blocks out of the lignocellulosic biorefinery feed. In this study, two scenarios for the biocatalytic Achmatowicz-type rearrangement using methanol as terminal sacrificial reagent have been evaluated, comparing multienzymatic cascade designs with a photo-bio-coupled activation pathway.",

keywords = "aerobic, enzymatic, furans, oxygenation, ring expansion, visible light",

author = "Christina J{\"a}ger and Clo{\'e} Bruneau and Wagner, {Philip K.} and Prechtl, {Martin H.G.} and Jan Deska",

note = "Funding Information: The authors gratefully acknowledge financial support by the Academy of Finland (298250, 309909 & 324976, JD) and the German Academic Exchange Service DAAD (MP) CJ thanks the Aalto School of Chemical Technology, as well as the Finnish Foundation for Technology Promotion and the Orion Research Foundation sr for personal grants. Publisher Copyright: {\textcopyright} Copyright {\textcopyright} 2021 J{\"a}ger, Bruneau, Wagner, Prechtl and Deska. Copyright: Copyright 2021 Elsevier B.V., All rights reserved.",

year = "2021",

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doi = "10.3389/fchem.2021.635883",

language = "English",

volume = "9",

journal = "Frontiers in Chemistry",

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AU - Jäger, Christina

AU - Bruneau, Cloé

AU - Wagner, Philip K.

AU - Prechtl, Martin H.G.

AU - Deska, Jan

N1 - Funding Information: The authors gratefully acknowledge financial support by the Academy of Finland (298250, 309909 & 324976, JD) and the German Academic Exchange Service DAAD (MP) CJ thanks the Aalto School of Chemical Technology, as well as the Finnish Foundation for Technology Promotion and the Orion Research Foundation sr for personal grants. Publisher Copyright: © Copyright © 2021 Jäger, Bruneau, Wagner, Prechtl and Deska. Copyright: Copyright 2021 Elsevier B.V., All rights reserved.

PY - 2021/4/7

Y1 - 2021/4/7

N2 - The oxidative ring expansion of bio-derived furfuryl alcohols to densely functionalized six-membered O-heterocycles represents an attractive strategy in the growing network of valorization routes to synthetic building blocks out of the lignocellulosic biorefinery feed. In this study, two scenarios for the biocatalytic Achmatowicz-type rearrangement using methanol as terminal sacrificial reagent have been evaluated, comparing multienzymatic cascade designs with a photo-bio-coupled activation pathway.

AB - The oxidative ring expansion of bio-derived furfuryl alcohols to densely functionalized six-membered O-heterocycles represents an attractive strategy in the growing network of valorization routes to synthetic building blocks out of the lignocellulosic biorefinery feed. In this study, two scenarios for the biocatalytic Achmatowicz-type rearrangement using methanol as terminal sacrificial reagent have been evaluated, comparing multienzymatic cascade designs with a photo-bio-coupled activation pathway.

KW - aerobic

KW - enzymatic

KW - furans

KW - oxygenation

KW - ring expansion

KW - visible light

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DO - 10.3389/fchem.2021.635883

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AN - SCOPUS:85104686132

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JO - Frontiers in Chemistry

JF - Frontiers in Chemistry

SN - 2296-2646

M1 - 635883

ER -

Methanol-Driven Oxidative Rearrangement of Biogenic Furans – Enzyme Cascades vs. Photobiocatalysis

Abstract

Keywords

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MOCCA: Molybdenum Catalysts for C1-Carbon Valorisation

Beyond Biosynthesis: Enzymes as Catalysts in Non-natural Synthetic Transformations

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Methanol-Driven Oxidative Rearrangement of Biogenic Furans – Enzyme Cascades vs. Photobiocatalysis

Abstract

Keywords

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Projects

MOCCA: Molybdenum Catalysts for C1-Carbon Valorisation

Beyond Biosynthesis: Enzymes as Catalysts in Non-natural Synthetic Transformations

Cite this