Title

Total Syntheses of Derivatives of Protoporphyrin IX Regioselectively Labeled with Carbon-13 in the Methyls

Document Type

Article

Publication Date

1-1-1986

Abstract

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

First Page

4667

Last Page

4676

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