Fully Biocatalytic Rearrangement of Furans to Spirolactones

Yu-Chang Liu; J. D. Rolfes; Joel Björklund; Jan Deska

doi:10.1021/acscatal.3c00132

Fully Biocatalytic Rearrangement of Furans to Spirolactones

Yu-Chang Liu^*, J. D. Rolfes, Joel Björklund, Jan Deska^*

^*Corresponding author for this work

Department of Chemistry and Materials Science

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

4 Citations (Scopus)

27 Downloads (Pure)

Abstract

A multienzymatic pathway enables the preparation of optically pure spirolactone building blocks. In a streamlined one-pot reaction cascade, the combination of chloroperoxidase, an oxidase, and an alcohol dehydrogenase renders an efficient reaction cascade for the conversion of hydroxy-functionalized furans to the spirocyclic products. The fully biocatalytic method is successfully employed in the total synthesis of the bioactive natural product (+)-crassalactone D, and as the key module in a chemoenzymatic route yielding lanceolactone A.

Original language	English
Pages (from-to)	7256-7262
Number of pages	7
Journal	ACS Catalysis
Volume	13
Issue number	11
Early online date	15 May 2023
DOIs	https://doi.org/10.1021/acscatal.3c00132
Publication status	Published - 2 Jun 2023
MoE publication type	A1 Journal article-refereed

Keywords

biocatalytic
cascade catalysis
cyclization
furans
multienzymatic
rearrangement
spirolactone

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1021/acscatal.3c00132Licence: CC BY

CHEM_Liu_et_al_Fully_Biocatalytic_2023_ACS_CatalysisFinal published version, 2.45 MBLicence: CC BY

Cite this

@article{0df0d53246dd4cc594a79d9fb6c14d01,

title = "Fully Biocatalytic Rearrangement of Furans to Spirolactones",

abstract = "A multienzymatic pathway enables the preparation of optically pure spirolactone building blocks. In a streamlined one-pot reaction cascade, the combination of chloroperoxidase, an oxidase, and an alcohol dehydrogenase renders an efficient reaction cascade for the conversion of hydroxy-functionalized furans to the spirocyclic products. The fully biocatalytic method is successfully employed in the total synthesis of the bioactive natural product (+)-crassalactone D, and as the key module in a chemoenzymatic route yielding lanceolactone A.",

keywords = "biocatalytic, cascade catalysis, cyclization, furans, multienzymatic, rearrangement, spirolactone",

author = "Yu-Chang Liu and Rolfes, {J. D.} and Joel Bj{\"o}rklund and Jan Deska",

note = "| openaire: EC/H2020/865885/EU//ABIONYS Funding Information: We gratefully acknowledge financial support of this study by the European Research Council (865885 (J.D.)), the Academy of Finland (298250 (J.D.) & 324854 (Y.C.L.)), the Ruth & Nils-Erik Stenb{\"a}cks Stiftelse (J.D.), and the Novo Nordisk Fonden (NNF17OC0025092 (Y.C.L.)). We also thank the Max-Planck-Institut f{\"u}r Kohlenforschung for the generous supply of computational resources and Sami Heikkinen for the assistance with the NMR spectroscopy. Publisher Copyright: {\textcopyright} 2023 The Authors. Published by American Chemical Society.",

year = "2023",

month = jun,

day = "2",

doi = "10.1021/acscatal.3c00132",

language = "English",

volume = "13",

pages = "7256--7262",

journal = "ACS Catalysis",

issn = "2155-5435",

publisher = "American Chemical Society",

number = "11",

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TY - JOUR

T1 - Fully Biocatalytic Rearrangement of Furans to Spirolactones

AU - Liu, Yu-Chang

AU - Rolfes, J. D.

AU - Björklund, Joel

AU - Deska, Jan

N1 - | openaire: EC/H2020/865885/EU//ABIONYS Funding Information: We gratefully acknowledge financial support of this study by the European Research Council (865885 (J.D.)), the Academy of Finland (298250 (J.D.) & 324854 (Y.C.L.)), the Ruth & Nils-Erik Stenbäcks Stiftelse (J.D.), and the Novo Nordisk Fonden (NNF17OC0025092 (Y.C.L.)). We also thank the Max-Planck-Institut für Kohlenforschung for the generous supply of computational resources and Sami Heikkinen for the assistance with the NMR spectroscopy. Publisher Copyright: © 2023 The Authors. Published by American Chemical Society.

PY - 2023/6/2

Y1 - 2023/6/2

N2 - A multienzymatic pathway enables the preparation of optically pure spirolactone building blocks. In a streamlined one-pot reaction cascade, the combination of chloroperoxidase, an oxidase, and an alcohol dehydrogenase renders an efficient reaction cascade for the conversion of hydroxy-functionalized furans to the spirocyclic products. The fully biocatalytic method is successfully employed in the total synthesis of the bioactive natural product (+)-crassalactone D, and as the key module in a chemoenzymatic route yielding lanceolactone A.

AB - A multienzymatic pathway enables the preparation of optically pure spirolactone building blocks. In a streamlined one-pot reaction cascade, the combination of chloroperoxidase, an oxidase, and an alcohol dehydrogenase renders an efficient reaction cascade for the conversion of hydroxy-functionalized furans to the spirocyclic products. The fully biocatalytic method is successfully employed in the total synthesis of the bioactive natural product (+)-crassalactone D, and as the key module in a chemoenzymatic route yielding lanceolactone A.

KW - biocatalytic

KW - cascade catalysis

KW - cyclization

KW - furans

KW - multienzymatic

KW - rearrangement

KW - spirolactone

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U2 - 10.1021/acscatal.3c00132

DO - 10.1021/acscatal.3c00132

M3 - Article

AN - SCOPUS:85160815693

SN - 2155-5435

VL - 13

SP - 7256

EP - 7262

JO - ACS Catalysis

JF - ACS Catalysis

IS - 11

ER -

Fully Biocatalytic Rearrangement of Furans to Spirolactones

Abstract

Keywords

UN SDGs

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ABIONYS: Artificial Enzyme Modules as Tools in a Tailor-made Biosynthesis

CEVALOR: Cellular factories for the valorization of biorefinery chemicals

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

Cite this

Fully Biocatalytic Rearrangement of Furans to Spirolactones

Abstract

Keywords

UN SDGs

Access to Document

Other files and links

Fingerprint

Projects

ABIONYS: Artificial Enzyme Modules as Tools in a Tailor-made Biosynthesis

CEVALOR: Cellular factories for the valorization of biorefinery chemicals

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

Cite this