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Biosynthesis of Porphyrins and Related Macrocycles. Part 16. Proof that the Single Intramolecular Rearrangement leading to Natural Porphyrins (Type-III) occurs at the Tetrapyrrole Level

DOI: 10.1039/P19810002786

Source and publish data:

Journal of the Chemical Society. Perkin transactions I p. 2786 - 2799 (1981)

Update date:2022-08-04

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Authors:

Battersby, Alan R.Battersby, Alan R.

Fookes, Christopher J. R.Fookes, Christopher J. R.

Meegan, Mary J.Meegan, Mary J.

McDonald, EdwardMcDonald, Edward

Wurziger, Hanns K. W.Wurziger, Hanns K. W.

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Article abstract of DOI:10.1039/P19810002786

The unrearranged aminomethylbilane (2) is synthesised by a rational route and is proved to be converted by the enzymes deaminase and cosynthetase, working co-operatively, into uro'gen-III (3).The single rearrangement step established earlier is thus proved to take place at the tetrapyrrole level.Synthesis of singly 13C-labelled bilane (2) followed by its enzymic conversion into uro'gen-III serves to register each of the pyrrole rings of the product relative to the initial bilane.Finally, methods for synthesis of the bilane are developed in two different doubly 13C-labelled forms to allow the following key points to be established largely by 13C n.m.r. spectroscopy: (a) as the bilane system is converted into uro'gen-III, intramolecular rearrangement of the terminal ring D occurs, and (b) the linear tetrapyrrole is converted intact into uro'gen-III.Syntheses of <15-13C>-, and <20-13C>-uroporphyrin octamethyl ester are described together with improved h.p.l.c. conditions for the separation of isomeric coproporphyrin tetramethyl esters.

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Product name:ethyl 4-t-butoxycarbonyl-3-(2-ethoxycarbonylethyl)-5-methyl<5-13C>pyrrole-2-carboxylate

Cas No:80504-94-5

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