On the Biosynthesis of Heme and Vitamin B 12 from [α,γ‐ 14 C 2 ]Uroporphyrinogen III
1972; Wiley; Volume: 11; Issue: 5 Linguagem: Inglês
10.1002/anie.197204211
ISSN1521-3773
AutoresBurchard Franck, Dietrich Gantz, Franz‐Peter Montforts, Franz P. Schmidtchen,
Tópico(s)Neonatal Health and Biochemistry
ResumoAngewandte Chemie International Edition in EnglishVolume 11, Issue 5 p. 421-422 Communication On the Biosynthesis of Heme and Vitamin B12 from [α,γ-14C2]Uroporphyrinogen III Prof. Dr. Burchard Franck, Prof. Dr. Burchard Franck Organisch-Chemisches Institut der Universität, 44 Münster, Orléans-Ring 23 (Germany)Search for more papers by this authorDr. Dietrich Gantz, Dr. Dietrich Gantz Organisch-Chemisches Institut der Universität, 44 Münster, Orléans-Ring 23 (Germany)Search for more papers by this authorDipl.-Chem. Franz-Peter Montforts, Dipl.-Chem. Franz-Peter Montforts Organisch-Chemisches Institut der Universität, 44 Münster, Orléans-Ring 23 (Germany)Search for more papers by this authorDipI-Chem. Franz Schmidtchen, Corresponding Author DipI-Chem. Franz Schmidtchen Organisch-Chemisches Institut der Universität, 44 Münster, Orléans-Ring 23 (Germany)Organisch-Chemisches Institut der Universität, 44 Münster, Orléans-Ring 23 (Germany)Search for more papers by this author Prof. Dr. Burchard Franck, Prof. Dr. Burchard Franck Organisch-Chemisches Institut der Universität, 44 Münster, Orléans-Ring 23 (Germany)Search for more papers by this authorDr. Dietrich Gantz, Dr. Dietrich Gantz Organisch-Chemisches Institut der Universität, 44 Münster, Orléans-Ring 23 (Germany)Search for more papers by this authorDipl.-Chem. Franz-Peter Montforts, Dipl.-Chem. Franz-Peter Montforts Organisch-Chemisches Institut der Universität, 44 Münster, Orléans-Ring 23 (Germany)Search for more papers by this authorDipI-Chem. Franz Schmidtchen, Corresponding Author DipI-Chem. Franz Schmidtchen Organisch-Chemisches Institut der Universität, 44 Münster, Orléans-Ring 23 (Germany)Organisch-Chemisches Institut der Universität, 44 Münster, Orléans-Ring 23 (Germany)Search for more papers by this author First published: May 1972 https://doi.org/10.1002/anie.197204211Citations: 28AboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onEmailFacebookTwitterLinkedInRedditWechat No abstract is available for this article. References 1 D. Shemin, Naturwissenschaften 57, 185 (1970); J. H. Mathewson and A. H. Corwin, J. Amer. Chem. Soc. 83, 135 (1961); L. Bogorad and R. F. Troxler in P. Bernfeld: Biogenesis of Natural Compounds. 2nd Edit., Pergamon Press, Oxford 1967, p. 247. 2 R. A. Neve, R. F. Labbe, and R. A. Aldrich, J. Amer. Chem. Soc. 78, 691 (1956); D. Mauzerall and S. Granick, J. Biol. Chem. 232, 1141 (1958); B. F. Burnham and R. A. Plane, Biochem. J. 98, 13c (1966). 3 D. Shemin and C. S. Russell, J. Amer. Chem. Soc. 75, 4873 (1953); S. Schwartz, K. Ikeda, I. M. Miller, and C. J. Watson, Science 129, 40 (1959); C. Bray and D. Shemin, J. Biol. Chem. 238, 1501 (1963). 4 B. Franck, D. Gantz, and F. Hüper, Angew. Chem. 84, 432 (1972); Angew. Chem. internat. Edit. 11, 420 (1972). 5 S. Granick, J. Biol. Chem. 232, 1101 (1958). 6 Obtained from [α, γ-14C2]uroporphyrin III octamethyl ester (5) [4] by hydrolysis of the ester groups by 20%. aqueous HCl at 20 o C and subsequent reduction by 2.5%. sodium amalgam in aqueous solution. 7 Spec. radioactivity of the isolated radioactive hemin divided by that of the [α, γ-14C2]uroporphyrinogen III fed and multiplied by 100. 8 Total radioactivity of the isolated radioactive hemin divided by that of the [α, γ-14C2]uroporphyrinogen III fed and multiplied by 100. 9 E. g. uroporphyrinogens isomerize easily in acid solution: L. Bogorod and G. S. Marks, J. Biol. Chem. 235, 2127 (1960); D. Mauzerall, J. Amer. Chem. Soc. 82, 2602 (1960). 10 M. W. Roomi and S. F. MacDonald, Canad. J. Chem. 48, 139 (1970); R. A. Chapman, M. W. Roomi, T. C. Morton, D. T. Krajcarski, and S. F. MacDonald, Canad. J. Chem. 49, 3544 (1971). 11 J. Wibaut J. Chim. Physique 53, 143 (1956). 12 Isolated as 2,4-dinitrophenylosazone. 13 The observed spec. radioactivities of the degradation products were referred to that of the isolated radioactive hemin (7) with two 14C atoms. Since in the degradation of the hemin the radioactivity of the α- and λ-methine groups is divided between two molecules each of the phyllopyrrole (9) and the methyl phyllopyrrolecarboxylate (11), these degradation products should each contain 25%. of the radioactivity of the hemin. The methyl 4,5-dioxohexanoate (13) can contain only a fraction of the radioactivity of the λ-methine group of (7) since in the ozonolysis of (11) it is formed mainly by fission according to a and only to a slight extent according to b and c. 14 J. D. Speedie and G. W. Hull, US-Pat. 2951107 (1960); Chem. Abstr. 54, 15852i (1960). 15 United States Pharmacopeia 15, 885 (1955); Internal report Difco Laboratories: Microbiological Assay of Vitamins and Amino Acids. Difco Company, Detroit 1964, p. 17. 16 After conclusion of our feeding experiments G. Müller and W. Dieterle, Hoppe-Seylers Z. physiol. Chem. 352, 143 (1971), announced that, using a biosynthetically obtained mixture of uniformly 14 C-labeled uroporphyinogens I and III and cell suspensions of Propionibacterium shermanii, they too observed no incorporation into the corrin ring of vitamin B12. Citing Literature Volume11, Issue5May 1972Pages 421-422 ReferencesRelatedInformation
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