On the Mechanism of Decarboxylation of Betanidine. A Contribution to the Interpretation of the Biosynthesis of Betalaines

descriptionPublicationkeyboard_double_arrow_right Article 31 Jan 1972 English Publisher:WileyJournal:Helvetica Chimica Acta, volume 55, pages 642-648 (issn: 0018-019X, eissn: 1522-2675,

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Authors: E, Dunkelblum; H E, Miller; A S, Dreiding;

doi: 10.1002/hlca.19720550239

pmid: 5023155

On the Mechanism of Decarboxylation of Betanidine. A Contribution to the Interpretation of the Biosynthesis of Betalaines

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Abstract

AbstractBei der Biogenese des Betanins (2) aus Dopa (1) wird die Carboxylgruppe der Aminosäure in die Carboxylgruppe‐C(19) umgewandelt. Dieser Schluss beruht auf einem Deuterierungsversuch, bei dem gezeigt wird, dass die Monodecarboxylierung von Betanidin (3) zu einem Verlust von C(19) führt und dass dabei die Doppelbindung C(17)C(18) nach C(14)C(15) wandert. Wenn radioaktives Betanidin (3), erhalten aus Einbauexperimenten mit DL‐Dopa‐[1‐14C], in Äthanol decarboxyliert wird, erhält der danach isolierte Dimethylester 7 des Decarboxybetanidin (6)‐hydrochlorids nur noch 14% des 14C.Bei der alkali‐katalysierten Äquilibrierung von Betanidin (3) ⇆ Isobetanidin (9) tritt im Gegensatz zur Decarboxylierung keine Wanderung der Doppelbindung ein.

Related Organizations

University of Zurich
Switzerland
National Institutes of Health
United States

Keywords

Carbon Isotopes, Chemistry, Chemical Phenomena, Pigments, Biological, Decarboxylation, Dihydroxyphenylalanine

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