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Biosynthesis of Porphyrins and Related Macrocycles. Part 14. Studies with Isoporphobilinogen and Four Isomeric Labelled Pyrromethanes: Specific Conversion of the Unrearranged Pyrromethane (+)NH3.AP.AP into Haem and Protoporphyrin-IX

DOI: 10.1039/P19810002771

Source and publish data:

Journal of the Chemical Society. Perkin transactions I p. 2771 - 2778 (1981)

Update date:2022-07-29

Topics:

Authors:

Battersby, Alan R.Battersby, Alan R.

Beck, John F.Beck, John F.

Gibson, Keith H.Gibson, Keith H.

Hodgson, Gordon L.Hodgson, Gordon L.

Markwell, Roger E.Markwell, Roger E.

at al.at al.

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Article abstract of DOI:10.1039/P19810002771

<11-14C>Isoporphobilinogen and 14C-, and 13C-labelled forms of four isomeric pyrromethanes have been synthesised in order to study at what stage in the building process rearrangement occurs to produce the natural porphyrins.The finding that isoporphobilinogen is not a biosynthetic precursor of protoporphyrin-IX points against the rearrangement being at the monopyrrole level.Of the four pyrromethanes, only the unrearranged system (+)NH3.AP.AP (5) is significantly converted, in the presence of the necessary enzymes from Euglena gracilis or duck's blood, into protoporphyrin-IX or haem.Degradation of these products from 14C-labelled (5) proved that the conversion of (+)NH3.AP.AP into the type-III macrocycle occurs without randomisation of the labels; this conclusion was rigorously confirmed by 13C-n.m.r. spectra from samples of 13C-protoporphyrin-IX produced enzymatically from 13C-labelled (5).

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