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 ) [V Br PO( An I)] was retained with a half-life time of ~60 days, if stored in H 2 O 2 -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 H 2 O 2 , KBr, and V Br PO( An I) in phosphate-buffered, CH 3 CN-diluted media.