Transition metal cations catalyze 16O/18O exchange of catechol motifs with H218O

Roelant Hilgers; Judith Bijlsma; Luana Malacaria; Jean Paul Vincken; Emilia Furia; Wouter J.C. de Bruijn

doi:10.1039/d2ob01884e

Transition metal cations catalyze ¹⁶O/¹⁸O exchange of catechol motifs with H₂¹⁸O

Roelant Hilgers, Judith Bijlsma, Luana Malacaria, Jean Paul Vincken, Emilia Furia, Wouter J.C. de Bruijn^*

^*Corresponding author for this work

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

2 Citations (Scopus)

Abstract

Catechol motifs are ubiquitous in nature, as part of plant, animal and microbial metabolites, and are known to form complexes with various metal cations. Here, we report for the first time that complexation with transition metal cations, especially Fe(iii), results in rapid ¹⁶O/¹⁸O exchange of the catecholic hydroxyl groups with H₂¹⁸O. We discuss the implications of this finding for mechanistic studies using H₂¹⁸O and potential relevance for production of ¹⁸O-labeled catechol derivatives.

Original language	English
Pages (from-to)	9093-9097
Journal	Organic and Biomolecular Chemistry
Volume	20
DOIs	https://doi.org/10.1039/d2ob01884e
Publication status	Published - 14 Dec 2022

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title = "Transition metal cations catalyze 16O/18O exchange of catechol motifs with H218O",

abstract = "Catechol motifs are ubiquitous in nature, as part of plant, animal and microbial metabolites, and are known to form complexes with various metal cations. Here, we report for the first time that complexation with transition metal cations, especially Fe(iii), results in rapid 16O/18O exchange of the catecholic hydroxyl groups with H218O. We discuss the implications of this finding for mechanistic studies using H218O and potential relevance for production of 18O-labeled catechol derivatives.",

author = "Roelant Hilgers and Judith Bijlsma and Luana Malacaria and Vincken, {Jean Paul} and Emilia Furia and {de Bruijn}, {Wouter J.C.}",

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T1 - Transition metal cations catalyze 16O/18O exchange of catechol motifs with H218O

AU - Hilgers, Roelant

AU - Bijlsma, Judith

AU - Malacaria, Luana

AU - Vincken, Jean Paul

AU - Furia, Emilia

AU - de Bruijn, Wouter J.C.

PY - 2022/12/14

Y1 - 2022/12/14

N2 - Catechol motifs are ubiquitous in nature, as part of plant, animal and microbial metabolites, and are known to form complexes with various metal cations. Here, we report for the first time that complexation with transition metal cations, especially Fe(iii), results in rapid 16O/18O exchange of the catecholic hydroxyl groups with H218O. We discuss the implications of this finding for mechanistic studies using H218O and potential relevance for production of 18O-labeled catechol derivatives.

AB - Catechol motifs are ubiquitous in nature, as part of plant, animal and microbial metabolites, and are known to form complexes with various metal cations. Here, we report for the first time that complexation with transition metal cations, especially Fe(iii), results in rapid 16O/18O exchange of the catecholic hydroxyl groups with H218O. We discuss the implications of this finding for mechanistic studies using H218O and potential relevance for production of 18O-labeled catechol derivatives.

U2 - 10.1039/d2ob01884e

DO - 10.1039/d2ob01884e

M3 - Article

C2 - 36378241

AN - SCOPUS:85142538541

SN - 1477-0520

VL - 20

SP - 9093

EP - 9097

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

ER -

Transition metal cations catalyze 16O/18O exchange of catechol motifs with H218O

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Transition metal cations catalyze ¹⁶O/¹⁸O exchange of catechol motifs with H₂¹⁸O