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. ?,?-unsaturated alcohols furnished ?-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. © 2009 IUPAC, Publication date (Web): 29 June 2009.