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Synthesis 2023; 55(06): 1000-1006
DOI: 10.1055/s-0041-1738426
paper

Modular Synthesis of New Pyrroloquinoline Quinone Derivatives

Rachel Janßen
,
Violeta A. Vetsova
,
Dominik Putz
,
Peter Mayer
,
Lena J. Daumann  ∗
L.J.D. would like to acknowledge a grant from the Deutsche Forschungsgemeinschaft­ (Grant number: (DFG)-392552271).
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Abstract

Pyrroloquinoline quinone (PQQ) is an important cofactor of methanol dehydrogenases and glycose dehydrogenases. In addition, isolated PQQ is used as a central component in sensors and biomimetic complexes. The synthesis of PQQ derivatives is of interest for developing new alcohol oxidation catalysts and redox sensors. This work describes a modular synthesis for derivatives of PQQ bearing methyl and ketone groups instead of carboxylic acid moieties. These modifications reduce the possible coordination sites of PQQ for metal ions outside the protein environment.

Key words

redox cofactor - pyrroloquinoline quinone - alcohol oxidation - pincer ligand - natural product derivatives

Supporting Information

    Supporting information (NMR and summary of crystallographic data) for this article is available online at https://doi.org/10.1055/s-0041-1738426.
  • Supporting Information

Primary Data

    Primary Data (NMR, IR, MS and more detailed reaction procedures) accessible at the Chemotion Online Repository.https://dx.doi.org/10.14272/collection/RAJ_2022-08-25
  • Primary Data


Publication History

Received: 28 August 2022

Accepted after revision: 19 September 2022

Article published online:
07 November 2022

© 2022. Thieme. All rights reserved

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