13306-30-4

Upstream product

• 67-56-1 methanol 
• 59969-39-0 coproporphyrinogen lV 
• 60297-36-1 3-{5-[4-(2-Methoxycarbonyl-ethyl)-3-methyl-1H-pyrrol-2-ylmethyl]-4-methyl-1H-pyrrol-3-yl}-propionic acid methyl ester 
• 4792-10-3 3-{5-Formyl-2-[5-formyl-3-(2-methoxycarbonyl-ethyl)-4-methyl-1H-pyrrol-2-ylmethyl]-4-methyl-1H-pyrrol-3-yl}-propionic acid methyl ester 
• 76044-20-7 4,4'-diethyl-3,3'-dimethyl-2,2'-pyrromethane-5,5'-dicarboxylic acid 
• 111017-71-1 3,3'-dimethylpyrromethane-5,5'-dicarboxylic acid 
• 111017-73-3 4-(2-methoxycarbonylethyl)-3,3'-dimethylpyrromethane-5,5'-dicarboxylic acid 

Downstream Products

• 53365-83-6 3-(4,5-dimethyl-pyrrol-3-yl)-propionic acid methyl ester 
• 54474-51-0 methyl 2,4-dimethyl-3-pyrrolepropionate 
• 5522-66-7 3,3'-(3,7,12,17-tetramethyl-8,13-divinyl-21H,23H-porphine-2,18-diyl)-bis-propionic acid dimethyl ester 

Relevant academic research and scientific papers

Biosynthesis of Porphyrins and Related Macrocycles. Part 15. Chemical and Enzymic Formation of Uroporphyrinogen Isomers from Unrearranged Aminomethylpyrromethane: Separation of Isomeric Coproporphyrin Esters

The unrearranged pyrromethane (1) is transformed chemically mainly into uro'gen-I with a smaller amount of uro'gen-IV but only traces of uro'gen-III are formed.Uro'gen-I is produced via a tetrapyrrolic (bilane) intermediate and when the diaminase-cosynthetase enzyme system from Euglena gracilis is present, this intermediate is converted into uro'gen-III.The rearrangement step for this conversion has the same characteristics found earlier for the natural biosynthetic process from porphobilinogen.Pyrromethane (1) is not a direct biosynthetic precursor of uro'gen-III and reasons are advanced why this is understandable.Methods are developed based on high pressure liquid chromatography for the separation of all four isomeric coproporphyrin esters.

Synthetic and Biosynthetic Studies of Porphyrins. Part 7. The Action of Coproporphyrinogen Oxidase on Coproporphyrinogen-IV: Syntheses of Protoporphyrin-XIII, Mesoporphyrin XIII, and Related Tricarboxylic Porphyrins

Coproporphyrinogen-IV (2a) is converted by an enzyme system from chicken blood into a tricarboxylic porphyrinogen (2b) and protoporphyrinogen-XIII (2c).The corresponding porphyrins were isolated as their methyl esters (3b) and (3c) and their structures were deduced by mass and n.m.r. spectrometry (including the use of shift reagents).Confirmation of these conclusions was obtained by total synthesis of the new porphyrins by the MacDonald and ac-biladiene routes.The vinyl groups were introduced either via acetoxyethyl side-chains derived from precursor pyrroles, or by reduction and dehydration of acetyl groups inserted into the porphyrins during the final stages of the syntheses.Mesoporphyrin-XIII dimethyl ester (3m) and the ethyl analogue (3n) of the vinyl tripropionate porphyrin (3b) were also synthesized by the MacDonald route.

Biosynthesis of Porphyrins and Related Macrocycles. Part 13. Structure of the Protoporphyrin Isomer derived from Coproporphyrinogen lV by the Action of Beef-Liver Coproporphyrinogenase: Synthesis of Protoporphyrin Xlll

Coproporphyrinogen lV (8) is synthesised and is oxidatively decarboxylated by coproporphyrinogenase from beef-liver to produce, after aromatisation, a porphyrin proved to be protoporphyrin Xlll (11) by spectroscopy and by unambiquous synthesis; the synthesis route is described.A monovinylporphyrin, derived from an intermediate for the conversion (8) -> (11), is also isolated.The importance of these results for earlier biosynthetic studies with pyrromethanes is discussed.