155434-89-2Relevant academic research and scientific papers
Synthetic Studies on the Proposed Spiro Intermediate for Biosynthesis of the Natural Porphyrins: Inhibition of Cosynthetase
Stark, W. Marshall,Hart, Graham J.,Battersby, Alan R.
, p. 465 - 467 (1986)
A macrocyclic spiro-lactam is synthesised which closely resembles the spiro system proposed as a biosynthetic intermediate for uro'gen-III; this spiro-lactam powerfully inhibits cosynthetase, the enzyme responsible for forming uro'gen-III.
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.
