62562-76-9Relevant academic research and scientific papers
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
Al-Hazimi, Hassan M. G.,Jackson, Anthony H.,Knight, David W.,Lash, Timothy D.
, p. 265 - 276 (2007/10/02)
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.
Methyl Deuteration Reactions in Vinylporphyrins: Protoporphyrins IX, III, and XIII
Smith, Kevin M.,Parish, Daniel W.,Inouye, Warren S.
, p. 666 - 671 (2007/10/02)
Base-catalyzed deuteration of the methyl groups in protoporphyrin IX dimethyl ester (1) proceeds with differential deuteration; rate of deuteration, as measured by NMR spectroscopy of reaction products, follows the order 3-Me > 1-Me >5-Me >8-Me.A simple q
SYNTHESIS OF BILIVERDIN IXγ (PTEROBILIN)
Jackson, Anthony H.,Jenkins, Rhianydd M.,Jones, D. Michael,Matlin, Stephen A.
, p. 1849 - 1858 (2007/10/02)
Condensation of a bis(acetoxyethyl)pyrromethane dicarboxylic acid (11d) with a diformylpyrroketone (12b) afforded a bis(acetoxyethyl)-γ-meso-hydroxyporphyrin (13d) which was converted into the related bis(chloroethyl)-γ-benzoyloxyporphyrin (14f).The Zn complex of the latter was transformed by brief treatment with base, followed by chloromethylethyl ether into the zinc bis(chloroethyl)-γ-ethoxymethoxyporphyrin (20b).Dehydrochlorination with potassium t-butoxide in t-butanol, and acid catalysed demetallation and deprotection then afforded the somewhat unstable blue γ-oxyprotoporphyrin dimethyl ester (21).The Fe-complex of the latter readily underwent oxidative ring opening by aerial oxidation in pyridine, and after demetallation gave biliverdin IXγ (pterobilin) dimethyl ester (22).
Neighboring Group Participation in the Pyrrole Series
Smith, Kevin M.,Martynenko, Zoya,Pandey, Ravindra K.,Tabba, Hani D.
, p. 4296 - 4302 (2007/10/02)
With use of proton and carbon-13 NMR spectroscopy of deuterium- and carbon-13-labeled substrates, the transformation of certain (2-hydroxyethyl)pyrroles (4, 18, 21) into the corresponding (2-haloethyl)pyrroles (using thionyl chloride/pyridine or triphenyl
