期刊
TETRAHEDRON
卷 67, 期 22, 页码 4048-4054出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2011.04.010
关键词
Bromoperoxidase; Enzyme; Oxidation catalysis; Pyrrole; Bromination; Natural product; Steady state kinetics
资金
- Deutsche Bundesstiftung Umwelt [20008/982]
- NanoKat
Ester-, cyano-, and carboxamide-substituted 1H-pyrroles undergo electrophilic aromatic bromination, if treated with hydrogen peroxide and sodium bromide at pH 6.2 and 20 degrees C. Oxidation of bromide under such conditions is catalyzed by a vanadate(V)-dependent bromoperoxidase, in a substrate/enzyme ratio of 32-63 mu mol %. To obtain maximum yields of bromopyrroles (up to 91%) by spending least amount of substrates and catalyst, hydrogen peroxide and sodium bromide have to be added continuously to the enzyme and the 2-acceptor-substituted pyrrole (1.5 mmol) in a solution of morpholine-4-ethanesulfonic acid buffer. This technique was applied to prepare two marine natural products under biomimetic conditions, that is, methyl 4,5-dibromopyrrole-2-carboxylate (from Agelas oroides) and 4,5-dibromopyrrole-2-carboxamide (from Acanthella carteri). (C) 2011 Elsevier Ltd. All rights reserved.
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