Benylisoquinoline
From DrugPedia: A Wikipedia for Drug discovery
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1-Benzylisoquinoline is the structural backbone of many alkaloids with a wide variety of structures, including papaverine, codeine, morphine, apomorphine, berberine, protopine and tubocurarine. | 1-Benzylisoquinoline is the structural backbone of many alkaloids with a wide variety of structures, including papaverine, codeine, morphine, apomorphine, berberine, protopine and tubocurarine. | ||
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== Biosynthesis == | == Biosynthesis == | ||
Current revision
1-Benzylisoquinoline is the structural backbone of many alkaloids with a wide variety of structures, including papaverine, codeine, morphine, apomorphine, berberine, protopine and tubocurarine.
[edit] Biosynthesis
Plants producing benzylisoquinoline alkaloids have a common biosynthetic pathway, making use of two units of L-tyrosine. One tyrosine molecule is metabolised to dopamine which constitutes the isoquinoline part, while the benzylic part is mostly formed from tyramine, itself the decarboxylation product of tyrosine.
Many benzylisoquinolines have a methylated nitrogen atom as well as functional groups containing oxygen (-OH, -OCH3, -OCH2O-) in positions 6, 7, 3' and 4'. The latter come from the precursors mentioned above, namely tyrosine, dopamine and their derivatives.
[edit] Examples of benzylisoquinoline alkaloids
Papaverine
Apomorphine (one additional ring closure)
Morphine (two additional ring closures)
Berberine (one additional ring closure with incorporated N-methyl)
Protopine (with opened pyridine ring)
Tubocurarine (composed of two benzylisoquinoline units)
[edit] References
Benzylisoquinoline biosynthesis by cultivated plant cells and isolated enzymes
