66 コリン・ポルフィリン類の生合成(ポスター発表の部)

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概要

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• We have synthesized various types of ^<13>C, ^<18>O, ^<15>N and ^2H labeled δ-amino levulinic acid (ALA) and utilize these compounds in the study of biosynthesis of corrinoids and porphyrinoids. The biosynthesis of porphyrins were studied in Arthrobacter hyalinus by using stable isotope tracer techniques and hight-field NMR spectroscopy. [2-^<13>C]-isopropanol, [1-^<13>C]-glutamate and ^<13>C ALA were incorporated in uro'gen III. ^<15>N-ALA, ^<15>N-riboflavine and ^<15>N-potassium cyanide incorporated V.B_<12> showed ^<15>N signals on ^<15>N-NMR. These results supported that nitrogens of corrin ring were derived from ALA. Also, nucleoside and cyano group were derived from riboflavine and potassium cyanide. To clarify the origins of amide-nitrogen of V.B_<12> [1-^<13>C]-ALA and L-[amide-^<15>N] glutamine were administered to P.shermanii. The ^<13>C-NMR spectrum of the V.B_<12> subsequently isolated showed distinct ^<13>C-^<15>N coupling and isotope shift at six amide carbons. However, the C-57 amide carbon showed neither coupling, nor shift. Thus, it was concluded that the nitrogensof 6 amides of the side chain were derived from glutamine. Distinct isotop-shifted peaks were observed in the ^<13>C-NMR spectrum of uroporphyrin III octamethylester isolated after incorporation of [1-^<13>C, 1, 1, 4-^<18>O_3]-ALA. This indicates that undilution of ^<18>O occurred at the acethyl chain of A ring of uro'gen III. This result supports the assumption that the lactone formation of the A ring contraction, as proposed by Eschenmoser. Further more feeding experiment of ^<13>C-labeld ALA in 50% D_2O medium and that of ^<13>C, ^2H-doubly labeled ALA into bacteriochlorophyll showed α, β isotope-shifted peak atring carbons. In the ^<13>C-{^1H}{^2H} NMR spectrum of bacteriochlorophyll, the numbers of deuterium atoms directorly attached to ^<13>C carbons were observed as shifted signals.

• 天然有機化合物討論会の論文
• 1991-09-07

著者

• 水谷 稔

  Department of Medicinal Chemistry, Meiji College of Pharmacy

• 梶原 正宏

  明治薬大

• 岡崎 健男

  Department of Medicinal Chemistry, Meiji College of Pharmacy

• 水谷 稔

  明治薬大

• 岡崎 健男

  明治薬大

• 水谷 稔

  Department Of Medicinal Chemistry Meiji College Of Pharmacy

• 岡崎 健男

  Department Of Medicinal Chemistry Meiji College Of Pharmacy

• Okazaki Takeo

  Department Of Medicinal Chemistry Meiji College Of Pharmacy

関連論文

• Biosynthesis of Corrinoids and Porphyrinoids. VII. Uroporphyrins from Saccharopolyspora erythraea
• 97(P16) タキサジエンの合成研究(ポスター発表の部)
• P-54 コリン、ポルフィリン類の生合成(ポスター発表の部)
• Studies on the Biosynthesis of Corrinoids and Porphyrinoids. X. Biosynthetic Studies of Bacteriochlorophyll-a in Rhodopseudomonas spheroides : Incorporation of ^2H-, ^C- and ^N-Labeled Substrates and Origin of the Hydrogen Atoms
• 66 コリン・ポルフィリン類の生合成(ポスター発表の部)
• Studies of the Biosynthesis of Corrinoids and Porphyrinoids. IV. Biosynthesis of Chlorophyll in Euglena gracilis
• Direct Observation of Enzymatic Transformation of δ-Aminolevulinic Acid to Porphobilinogen and Uroporphyrinogen in a Cell-Free System by Carbon-13 Nuclear Magnetic Resonance Spectroscopy
• Studies on the Biosynthesis of Corrinoids and Porphyrinoids.II. : The Origin of Nitrogen of Vitamin B_
• 89(P2-19) クロロフィル・バクテリオクロロフィルの生合成(ポスター発表の部)
• Studies on the Biosynthesis of Corrinoids and Porphyrinoids. I : The Labeling of Oxygen of Vitamin B_
• 19 コリン・ポルフィリン類の生合成(ポスター発表の部)
• Studies on ^C-Phenacetin Metabolism. II. A Combination of Breath Test and Urine Test of in Vivo Metabolites in the Diagnosis of Liver Disease

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