Identification of tetrapyrrole compounds excreted by Rhodobacter sphaeroides and sources of the methyl hydrogens of bacteriochlorophyll a biosynthesized by R. sphaeroides, based on 13C-NMR spectral analysis of coproporphyrin III tetramethyl ester.
Red-fluorescent tetrapyrrole compounds excreted by Rhodobacter sphaeroides into the culture broth were concluded to be coproporphyrinogen (Copro'gen) III and uroporphyrinogen (Uro'gen) I, based on the (13)C-NMR spectral identification of coproporphyrin (Copro) III tetramethyl ester and uroproporphyrin (Uro) I octamethyl ester. The sources of the methyl hydrogens of bacteriochlorophyll a were established by analysis of the (13)C-NMR spectra of (2)H,(13)C-Copro III tetramethyl ester chemically derived from (2)H,(13)C-Copro'gen III biosynthesized through the feeding of delta-amino[2-(13)C]levulinic acid (ALA) to R. sphaeroides in medium containing 50% (2)H(2)O. We confirmed the previous finding that one of the methyl hydrogens was derived from water in the medium during decarboxylation of four acetyl side chains of Uro'gen III to generate Copro'gen III. It was further shown that the other hydrogen atoms, previously reported to be derived from methylene hydrogens at C-2 of ALA, had been exchanged with hydrogen of water in the medium in the biosynthetic pathways leading from ALA to Copro'gen III.
Iida
Katsumi
K
Department of Medicinal Chemistry, Meiji Pharmaceutical University, Noshio, Kiyose, Tokyo, Japan. iida@my-pharm.ac.jp
Nakamura
Masayuki
M
Hanamitsu
Hiroshi
H
Kajiwara
Masahiro
M
D000622:Aminolevulinic Acid / Q000031:analogs & derivatives / Q000737:chemistry; D025541:Bacteriochlorophyll A / Q000096:biosynthesis*; D002247:Carbon Isotopes; D002478:Cells, Cultured; D003305:Coproporphyrinogens / Q000378:metabolism; D003306:Coproporphyrins / Q000737:chemistry* / Q000378:metabolism; D004952:Esters / Q000737:chemistry* / Q000378:metabolism; D006859:Hydrogen / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008697:Methane / Q000737:chemistry; D015394:Molecular Structure; D012242:Rhodobacter sphaeroides / Q000378:metabolism*; D045725:Tetrapyrroles / Q000737:chemistry* / Q000302:isolation & purification*; D014577:Uroporphyrinogens / Q000378:metabolism
D025541:Bacteriochlorophyll A; D002247:Carbon Isotopes; D003305:Coproporphyrinogens; D003306:Coproporphyrins; D004952:Esters; D045725:Tetrapyrroles; D014577:Uroporphyrinogens; C114767:delta-aminolevulinic acid methyl ester; C026971:coproporphyrin III; C028026:coproporphyrinogen III; D006859:Hydrogen; D000622:Aminolevulinic Acid; D008697:Methane