Biosynthesis of reticuline

Bhakuni, Dewan S. ; Singh, Awadhesh N. ; Tewari, Shobha ; Kapil, Randhir S. (1977) Biosynthesis of reticuline Journal of Chemical Soceity, Perkin Transactions 1 . pp. 1662-1666. ISSN 0300-922X

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Official URL: http://www.rsc.org/publishing/journals/P1/article....

Related URL: http://dx.doi.org/10.1039/P19770001662

Abstract

The incorporation of tyrosine, dopa, dopamine, and 4-hydroxy- and 3,4-dihydroxy-phenylpyruvic acids into reticuline in Litsea glutinosa has been studied, and it has been demonstrated that dopa and dopamine contribute only to the formation of the phenethylamine portion; the benzylic portion is biosynthesized from 3,4-dihydroxyphenylpyruvic acid not derived from dopa. Tyrosine and 4-hydroxy- and 3,4-dihydroxy-phenylpyruvic acids participate in the formation of both halves of reticuline. Tracer experiments have shown the intermediacy of norlaudanosoline-1-carboxylic acid, norlaudanosoline, and didehydronorlaudanosoline in the biosynthesis of reticuline. Incorporation studies with (±)-4'-O-methylnorlaudanosoline, (±)-laudanosoline, (±)-6-O-methylnorlaudanosoline, and (±)-nor-reticuline have demonstrated that O-methylation prededes N-methylation and that there is no rigid selectivity of O-methylation in the biosynthesis of reticuline.

Item Type:Article
Source:Copyright of this article belongs to Royal Society of Chemistry.
ID Code:2354
Deposited On:07 Oct 2010 14:41
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