65038-94-0Relevant academic research and scientific papers
Synthetic and Biosynthetic Studies of Porphyrins.Part10.Syntheses of Porphyrins with Acetic,Propionic,and Butyric Acid Side-chains for Biosynthetic Syudies.
Jackson, Anthony H.,Pandey, Ravindra K.,Smith, Kevin M.
, p. 299 - 306 (2007/10/02)
In connection with studies of substrate specificity of uroporphyrinogen decarboxylase and coproporphyrinogen oxidase, enzymes in the heme and chlorophyll biosynthetic pathways,and heme oxygenase,an enzyme involved in the catabolism of hemes,we have synthesized a number of new porphyrins substituted with acetic,propionic,and butyric side-chains,using the a,c-biladiene route;one porphyrin was also prepared by the MacDonald pyrromethane approach.In one of the a,c-biladiene cyclizations,meso-chlorinated porphyrins were formed as minor by products,but this side-reaction was suppressed by carefully drying the copper(II) chloride used in this stage, or by use of copper(II) acetate as an alternative oxidant.
Sapphyrins: Novel Aromatic Pentapyrrolic Macrocycles
Bauer, Victor J.,Clive, Derrick L.J.,Dolphin, David,Paine, John B.,Harris, Francis L.,et al.
, p. 6429 - 6436 (2007/10/02)
Sapphyrins are pentapyrrolic macrocycles containing one direct link and four bridging methine groups between the five pyrrolic subunits.The syntheses of decamethylsapphyrin, other peripherally alkylated derivatives, and metal complexes are described.The p
Syntheses of Methyl-devinylporphyrins Related to Protoporphyrin -IX. Initial Studies on the Mechanism of the Copper(II) Catalysed Cyclization of 1',8'-Dimethyl-a,c-biladiene Salts
Smith, Kevin M.,Kehres, Lisa A.
, p. 2329 - 2335 (2007/10/02)
Using copper(II) catalysed cyclization of a,c-biladiene dihydrobromide salts, porphyrins related to protoporphyrin-IX dimethyl ester (8), but in which both vinyls are replaced with methyls, or where either the 2- or 4-vinyls are individually replaced with methyls, are synthesized.These compounds are required for reconstitution of the corresponding hemes into hemoproteins, to enable the study of the rotational disorder of prosthetic heme groups in reconstituted hemoproteins.By way of 13C n.m.r. spectroscopy of enriched a,c-biladienes and porphyrins, the copper(II) catalysed cyclization of 1',8'-dimethyl-a,c-biladiene dihydrobromides is shown to afford porphyrins in which one of the 1'- and 8'-methyl groups becomes the new linking meso carbon atom.
