Thiols Act as Methyl Traps in the Biocatalytic Demethylation of Guaiacol Derivatives.

Simona Pompei, Christopher Grimm, Christine Schiller, Lukas Schober, Wolfgang Kroutil

Open access · hybridAbstract read

In one paragraph

Article in Angewandte Chemie (Weinheim an der Bergstrasse, Germany), 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 1 paper.

0numbers the graph read from it

0cells of the map it votes in

1citing papers in PubMed

–field-weighted citation impact, top 84% of its field

1 · What the graph read from it

What it found

Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.

The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.

2 · The registry

The trial behind it

Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.

Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.

3 · Its place in the literature

Who cites it

1 citing paper in PubMed, 0 citations in OpenAlex.

Thiols Act as Methyl Traps in the Biocatalytic Demethylation of Guaiacol Derivatives.Angewandte Chemie (Weinheim an der Bergstrasse, Germany) · 2021
Article

4 · The record

Corrections and comments

PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.

5 · Who and what money

Authors and funding

5 authors at 1 institution in 1 country.

Simona PompeiInstitute of Chemistry, Biocatalytic Synthesis University of Graz, NAWI Graz Heinrichstrasse 28 8010 Graz Austria.

Christopher GrimmInstitute of Chemistry, Biocatalytic Synthesis University of Graz, NAWI Graz Heinrichstrasse 28 8010 Graz Austria.

Christine SchillerInstitute of Chemistry, Biocatalytic Synthesis University of Graz, NAWI Graz Heinrichstrasse 28 8010 Graz Austria.

Lukas SchoberInstitute of Chemistry, Biocatalytic Synthesis University of Graz, NAWI Graz Heinrichstrasse 28 8010 Graz Austria.

Wolfgang KroutilInstitute of Chemistry, Biocatalytic Synthesis University of Graz, NAWI Graz Heinrichstrasse 28 8010 Graz Austria.ORCID 0000-0002-2151-6394

University of Graz · AT

Funding

Austrian Science Fund FWF P 30920

6 · The paper itself

Abstract

Demethylating methyl phenyl ethers is challenging, especially when the products are catechol derivatives prone to follow-up reactions. For biocatalytic demethylation, monooxygenases have previously been described requiring molecular oxygen which may cause oxidative side reactions. Here we show that such compounds can be demethylated anaerobically by using cobalamin-dependent methyltransferases exploiting thiols like ethyl 3-mercaptopropionate as a methyl trap. Using just two equivalents of this reagent, a broad spectrum of substituted guaiacol derivatives were demethylated, with conversions mostly above 90 %. This strategy was used to prepare the highly valuable antioxidant hydroxytyrosol on a one-gram scale in 97 % isolated yield.

Indexed as

biotransformationcobalamin-dependent enzymesdemethylationmethyl phenyl ethersthioethers

Identifiers

PMID38505659

DOI10.1002/ange.202104278

PMCPMC10946705

OpenAlexW4252057782

What OpenQuestion holds

Textmetadata

LicenceCC BY

Read underepoch 390

Registered trials

None linked

Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.