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Tetrapyrroles: the pigments of life.
How nature builds the pigments of life: the conquest of vitamin B12.
An interdisciplinary attack was needed that allowed the step-by-step synthetic pathway of B12 to be elucidated, and this approach has acted as a model for future research on the synthesis of substances in living organisms. Expand
Biosynthesis of the natural porphyrins: experiments on the ring-closure steps and with the hydroxy-analogue of porphobilinogen
Experiments on the conversion of porphobilinogen PBG (1) into uro'gens support formation of the pyrrolenine (4) which, at least for production of uro'gen-I (9), is converted next into theExpand
Vitamin B12: How the Problem of Its Biosynthesis Was Solved
Vitamin B12 is an essential vitamin for human health, and lack of it leads to pernicious anemia. This biological activity has attracted intense interest for some time; in addition, the complexExpand
Proof by synthesis that unrearranged hydroxymethylbilane is the product from deaminase and the substrate for cosynthetase in the biosynthesis of uro'gen-III
The labile unrearranged hydroxymethylbilane (5) is synthesised unambiguously, is proved to be identical with the product from deaminase acting on porphobilinogen, and is shown to be the substrate forExpand
Biosynthesis of the natural porphyrins: proof that hydroxymethylbilane synthase (porphobilinogen deaminase) uses a novel binding group in its catalytic action
Hydroxymethylbilane synthase builds a bilane by assembling 4 monopyrrolic units, the first of these being bound covalently to the enzyme through a group X; it is proved that X represents a uniqueExpand
Stereochemistry of biosynthesis of the vinyl groups of protoporphyrin-IX: a short synthesis of porphobilinogen
Porphobilinogen (1), [2H]-labelled in the propionic residue, is synthesised by a short route and is used to establish that both vinyl groups of protoporphyrin-IX are biosynthesised by overallExpand
Biosynthesis of porphyrins and related, macrocycles. Part 28. Development of a pulse labelling method to determine the C-methylation sequence for vitamin B12
The biosynthesis of vitamin B12 involves enzymic C-methylation of uroporphyrinogen-III at 8 sites. Earlier work had established that the first 3 methyl groups are introduced at positions 2, 7, and 20Expand
Biosynthesis of vitamin B12: isolation of 15,23-dihydrosirohydrochlorin, a biosynthetic intermediate: structural studies and incorporation experiments
An enzyme system from the vitamin B12 producer Propionibacterium shermanii converts uro'gen-III(2) into 15,23-dihydrosirohydrochlorin (7), the structure being established by 1H and 13C n.m.r.Expand