80504-89-8Relevant articles and documents
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
Battersby, Alan R.,Fookes, Christopher J. R.,Meegan, Mary J.,McDonald, Edward,Wurziger, Hanns K. W.
, p. 2786 - 2799 (2007/10/02)
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 -, and -uroporphyrin octamethyl ester are described together with improved h.p.l.c. conditions for the separation of isomeric coproporphyrin tetramethyl esters.