Total Syntheses of Derivatives of Protoporphyrin IX Regioselectively Labeled with Carbon-13 in the Methyls
Total syntheses, from monopyrroles via tripyrrenes and a,c-biladienes, of the four isomers 2–5 of protoporphyrin IX dimethyl ester in which the 1-, 3-, 5-, and 8-methyl groups are individually and regioselectively enriched with carbon-13 are described. The source of labeled carbon was 90% carbon-13-enriched paraformaldehyde, and methyls were inserted at the monopyrrole stage by reductive C-alkylation. The carbon-13-labeled porphyrins, as the corresponding hemes, are of interest as probes in carbon-13 NMR spectroscopic studies of reconstituted heme proteins. © 1986, American Chemical Society. All rights reserved.
Publication Source (Journal or Book title)
Journal of Organic Chemistry
Smith, K., Fujinari, E., Pandey, R., & Tabba, H. (1986). Total Syntheses of Derivatives of Protoporphyrin IX Regioselectively Labeled with Carbon-13 in the Methyls. Journal of Organic Chemistry, 51 (24), 4667-4676. https://doi.org/10.1021/jo00374a031