Manipulation of vinyl groups in protoporphyrin IX: introduction of deuterium and carbon-13 labels for spectroscopic studies

Porphyrin-Mediated Cell Surface Heme Capture from Hemoglobin byPorphyromonas gingivalis

“…The free acids of protoporphyrin isomers IV, VI, IX, XIII, XIV, and XII were prepared from the dimethyl ester analogues by following the method of Smith and coworkers (50). The general method is as follows.…”

“…5a, vertical twofold axes in the plane of the porphyrin rings) and each structure could be drawn flipped over. The competition with Hb binding determined by the solidphase assay demonstrated that the order of strength of the interaction with HA2 is as follows: PPIX ϭ PPIV ϭ PPXIII (IC 50 ϭ 6 to 15 M) Ͼ PPXIV (IC 50 ϭ 40 to 50 M) Ͼ PPXII (estimated range for IC 50 , 60 to 90 M; Fig. 5b) Ͼ PPVI (weak competition was observed [data not shown]; estimated IC 50 , Ͼ500 M).…”

Stereoselective in Vitro Formation of c-type Cytochrome Variants from Hydrogenobacter thermophilus Containing Only a Single Thioether Bond

“…Heme derivatives were synthesized as described previously (14). For the heme nomenclature the Fischer system of nomenclature is used.…”

Synthesis of the 6,7-bis[2-methoxycarbonyl(1,1- dideutero)-ethyl] derivative of protoporphyrin IX dimethyl ester

“…Dehydrohalogenation using potassium hydroxide in pyridine at refluxing temperature followed by diazomethane treatment gave the protoporphyrin IX dimethyl ester 25 in 70% yield. The resulting porphyrin was treated in the normal way [10] with ferrous chloride in methanol to give the hemin dimethyl ester 26, and finally the propionic ester functionalities were hydrolyzed using aqueous potassium hydroxide/methanol [10] to afford the desired hemin 27 in 80% overall yield.…”