Publications

Google Scholar

publications

Scopus

publications

ORCID

Dr. Caroline E. Paul

Pure

research output

Selected publications

Allison E. Wolder, Christian M. Heckmann, Peter-Leon Hagedoorn, Diederik J. Opperman, Caroline E. Paul*

Asymmetric Monoreduction of α,β-Dicarbonyls to α-Hydroxy Carbonyls by Ene Reductases

Ene reductases (EREDs) catalyze asymmetric reduction with exquisite chemo-, stereo-, and regioselectivity. Recent discoveries led to unlocking other types of reactivities toward oxime reduction and reductive C–C bond formation. Exploring nontypical reactions can further expand the biocatalytic knowledgebase, and evidence alludes to yet another variant reaction where flavin mononucleotide (FMN)-bound ERs from the old yellow enzyme family (OYE) have unconventional activity with α,β-dicarbonyl substrates. In this study, we demonstrate the nonconventional stereoselective monoreduction of α,β-dicarbonyl to the corresponding chiral hydroxycarbonyl, which are valuable building blocks for asymmetric synthesis.
C. M. Heckmann, M. Bürgler, C. E. Paul*

Peroxygenase-catalyzed allylic oxidation unlocks telescoped synthesis of (1S,3R)-3-hydroxycyclohexanecarbonitrile

ACS Catal. 2024, 14, 2985-2991. 10.1021/acscatal.4c00177
Enzymatic strategies for allylic oxidation are underdeveloped, with few examples on selected substrates with cytochrome P450s and unspecific peroxygenases (UPOs). In this case, UPOs were found to catalyze the desired allylic oxidation with high chemo- and regioselectivity, at substrate loadings of up to 200 mM, without the addition of organic cosolvents, thus enabling the subsequent ER and ADH steps in a three-step one-pot cascade. UPOs even displayed unreported enantioselective oxyfunctionalization and overoxidation of the substituted cyclohexene.
This synthetic approach provides the first example of a three-step, one-pot UPO-ER-ADH cascade and highlights the potential for UPOs to catalyze diverse enantioselective allylic hydroxylations and oxidations that are otherwise difficult to achieve.
Holly A. Reeve,* Jake Nicholson, Farieha Altaf, Thomas H. Lonsdale, Janina Preissler, Lars Lauterbach, Oliver Lenz, Silke Leimkuehler, Frank Hollmann, Caroline E. Paul* and Kylie A. Vincent*

A hydrogen-driven biocatalytic approach to recycling synthetic analogues of NAD(P)H

We demonstrate a recycling system for synthetic nicotinamide cofactor analogues using a soluble hydrogenase with turnover number of >1000 for reduction of the cofactor analogues by H2. Coupling this system to an ene reductase, we show quantitative conversion of N-ethylmaleimide to N-ethylsuccinimide. The biocatalyst system retained >50% activity after 7 h.
Caroline E. Paul, Daniel Eggerichs, Adrie H. Westphal, Dirk Tischler, Willem J.H. van Berkel

Flavoprotein monooxygenases: versatile biocatalysts

Flavoprotein monooxygenases (FPMOs) are single- or two-component enzymes that catalyze a diverse set of chemo-, regio- and enantioselective oxyfunctionalization reactions.
Lía Martínez-Montero, Dirk Tischler, Philipp Süss, Anett Schallmey, Maurice C. R. Franssen, Frank Hollmann and Caroline E. Paul*

Asymmetric azidohydroxylation of styrene derivatives mediated by a biomimetic styrene monooxygenase enzymatic cascade

We established a cascade for the asymmetric azidohydroxylation of styrene derivatives leading to chiral substituted 1,2-azido alcohols via enzymatic asymmetric epoxidation, followed by regioselective azidolysis, affording the azido alcohols with up to two contiguous stereogenic centers.
Ruud A. Weusthuis, Pauline L. Folch, Ana Pozo-Rodríguez, Caroline E.Paul

Applying non-canonical redox cofactors in fermentation processes

We propose to apply non-canonical redox cofactors (NRCs) in metabolic networks: cofactors that channel electrons exclusively from substrate to product, forming orthogonal circuits for electron transfer.

Flavoenzyme-mediated regioselective aromatic hydroxylation with coenzyme biomimetics

ChemCatChem 2020, 12, 1368–1375

A. Guarneri, A.H. Westphal, J. Leertouwer, J. Lunsonga, M.C.R. Franssen, D.J. Opperman, F. Hollmann, W.J.H. van Berkel, C.E. Paul*

Alternative coenzymes for biocatalysis

Curr. Opin. Biotechnol. 2019, 60, 63–71

A. Guarneri, W.J.H. van Berkel, C.E. Paul*

Synthetic biomimetic coenzymes and alcohol dehydrogenases for asymmetric catalysis

Catalysts 2019, 9, Article 207

L. Josa-Culleré, A.S.K. Lahdenperä, A. Ribaucourt, G.T. Höfler, S. Gargiulo, Y.-Y. Liu, J.-H. Xu, J. Cassidy, F. Paradisi, D.J. Opperman, F. Hollmann*, C.E. Paul*

Biocatalytic C=C bond reduction through carbon nanodot-sensitized regeneration of NADH analogues

Angew. Chem. Int. Ed. 2018, 57, 13825–13828
J. Kim, S.H. Lee, F. Tieves, D.S. Choi, F. Hollmann, C.E. Paul*, C.B. Park*

Old Yellow Enzyme-catalysed asymmetric hydrogenation: linking family roots with improved catalysis

Catalysts 2017, 7, Article 130

A. Scholtissek, D. Tischler, A.H. Westphal, W.J.H. van Berkel, C.E. Paul*

Dr. Caroline E. Paul

Associate Professor

email

Deel deze pagina: