104705-80-8Relevant academic research and scientific papers
Biosynthesis of porphyrins and related macrocycles. Part 48. The rearrangement of 2H-pyrroles (pyrrolenines) related to the proposed spiro-intermediate for porphyrin biosynthesis
Hawker, Craig J.,Spivey, Alan C.,Leeper, Finian J.,Battersby, Alan R.
, p. 1509 - 1517 (2007/10/03)
It is proposed that the biosynthesis of uroporphyrinogen III 3, the parent precursor of the natural porphyrins, chlorins and corrins, involves a 2H-pyrrole (pyrrolenine) 2 as a key intermediate. Model pyrrolenines have now been used to show that (a) pyrro
Biosynthesis of Porphyrins and Related Macrocycles. Part 40. Synthesis of a Spiro-lactam Related to the Proposed Spiro-Intermediate for Porphyrin Biosynthesis: Inhibition of Cosynthetase
Stark, W. Marshall,Hawker, Craig J.,Hart, Graham J.,Philippides, Athena,Petersen, Paul M.,et al.
, p. 2875 - 2892 (2007/10/02)
Routes are developed for synthesis of the tripyrrolic macrocyclic spiro-lactam 39.A minor product from the synthesis, thought earlier to be an atropisomer, has been shown by molecular mechanics calculations and re-investigation to be a dimer.The octa-acid derived from 39 closely resembles the spiro-pyrrolenine 2 proposed as a biosynthetic intermediate for uroporphyrinogen III.This octa-acid acts as a strong inhibitor of cosynthetase (uroporphyrinogen III synthase) whilst other similar systems which lack some of its functionality do not.These results strongly support the view that the spiro system 2 is indeed the biosynthetic intermediate for formation of uroporphyrinogen III 3 from hydroxymethylbilane 1.
