On the reactivity of bromoperoxidase I (Ascophyllum nodosum) in buffered organic media: Formation of carbon bromine bonds

Abstract

Peroxidase (PO) activity of vanadate(V)-dependent bromoperoxidase (BPO) I (Ascophyllum nodosum) [VBrPO(AnI)] was retained with a half-life time of ~60 days, if stored in H2O2-incubated, morpholin-4-ethane sulfonic acid (MES)-buffered aqueous alcoholic solutions. These conditions were applied for converting bromide and, e.g., methyl pyrrole-2-carboxylate into bromopyrroles with an almost quantitative peroxide yield. δ,ε-unsaturated alcohols furnished β-bromohydrins and products of bromocyclization, i.e., tetrahydrofurans and tetrahydropyrans (70–84 % mass balance), if treated with H2O2, KBr, and VBrPO(AnI) in phosphate-buffered, CH3CN-diluted media.

cis‐Dioxomolybdenum(VI) complexes with unsymmetric linear tetradentate ligands: syntheses, structures and bromoperoxidase activities

“…Haloperoxidases are capable of efficiently catalysing the halogenation of a variety of organic compounds in the presence of hydrogen peroxide and halides (Cl − , Br − and I − ) . Among halogenated organic compounds, brominated ones are of particular interest due to their extensive applications in the synthesis of flame retardants, pharmaceuticals, biocides and pesticides .…”

“…Among halogenated organic compounds, brominated ones are of particular interest due to their extensive applications in the synthesis of flame retardants, pharmaceuticals, biocides and pesticides . In recent times, because of its convenient and eco‐friendly nature, oxidative bromination with bromoperoxidases and their mimics has drawn considerable attention over traditional bromination using Br 2 . Vanadium(V)‐based bromoperoxidases are most widespread among all the naturally occurring bromoperoxidases .…”

“…In recent times, because of its convenient and eco‐friendly nature, oxidative bromination with bromoperoxidases and their mimics has drawn considerable attention over traditional bromination using Br 2 . Vanadium(V)‐based bromoperoxidases are most widespread among all the naturally occurring bromoperoxidases . As a result, complexes of oxovanadium(V) have been studied extensively as structural and functional models for bromoperoxidases .…”

Characterization of a Functional Vanadium-Dependent Bromoperoxidase in the Marine Cyanobacterium Synechococcus Sp. Cc93111

“…The hypobromous acid intermediate is generally thought to be freely dispersing. However, strong evidence supports specificity toward a final organic substrate (Butler and Carter-Franklin 2004, Kamenarska et al 2007, Hartung et al 2009).…”

“…However, strong evidence supports specificity toward a final organic substrate (Butler and Carter‐Franklin 2004, Kamenarska et al. 2007, Hartung et al. 2009).…”