On the Biosynthesis of 5-Methoxybenzimidazole. Precursor-Function of 5-Hydroxybenzimidazole, Benzimidazole and Riboflavin
- 1 August 1975
- journal article
- Published by Wiley in European Journal of Biochemistry
- Vol. 56 (2) , 427-432
- https://doi.org/10.1111/j.1432-1033.1975.tb02249.x
Abstract
1. In Clostridium thermoaceticum 5-hydroxybenzimidazole is methylated to 5-methoxybenz-imidaxole and transformed to 5-methoxybenzimidazolylcobamide. 5-Hydroxybenzimidazolycobamide is also methylated to 5-methoxybenzimidazolylcobamide. These results indicate a possible precursor function of 5-hydroxybenzimidazole in the biosynthesis of 5-methoxybenzimidazole. 2. The same microorganism uses benzimidazole to form benzimidazolylcobamide. This or externally added benzimidazolylcobamide, although taken up by the cells, is not further transformed (i.e. hydroxylated and methylated to 5-methoxybenzimdazolylcobamidel). This excludes a precursor function of benzimidazole in the biosynthesis of 5-methoxybenzimidazole. 3. Contrary to the biosynthesis of 5,6-dimethylbenzimidazole, 5-methoxybenzimidazole is not formed from riboflavin, but riboflavin inhibits the growth and the production of 5-methoxybenzimidazolylcobamide in Clostridium thermoaceticum. A tentative scheme for the biosynthesis of 5-methoxybenzimidazole via a riboflavin analog is discussed.Keywords
This publication has 19 references indexed in Scilit:
- Photolumazines, new naturally occurring inhibitors of riboflavin synthetaseBiochimica et Biophysica Acta (BBA) - General Subjects, 1973
- Biosynthesis of 5, 6‐dimethylbenzimidazole from riboflavin Transformation of C‐1′ of riboflavin into C‐2 of 5, 6‐dimethylbenzimidazoleFEBS Letters, 1972
- Biosynthesis of 5,6-dimethylbenzimidazole from 6,7-dimethyl-14C-8-ribityllumazineBiochemistry, 1971
- The biosynthesis of 5,6-dimethylbenzimidazole from 6,7-Di[14C]methyl-8-ribityl-lumazineJournal of the Chemical Society D: Chemical Communications, 1971
- Riboflavin as precursor in the biosynthesis of the 5,6‐Dimethylbenzimidazole‐moiety of vitamin B12FEBS Letters, 1970
- Beiträge zur Chemie und Biochemie der „Cobalamine”︁, II. Mitteil.: Über den Abbau der „Cobalamine”︁ mit Cer (III)‐hydroxyd. 7‐[ D ‐Ribofuranosido]‐adenin, ein Abbauprodukt des Pseudovitamins B 12European Journal of Inorganic Chemistry, 1956
- Beiträge zur Chemie und Biochemie der „Cobalamine”︁, I. Mitteil.:Über die Alkylierung von B12‐Faktor III und Vitamin B12European Journal of Inorganic Chemistry, 1956
- Purine studies. Part II. The ultra-violet absorption spectra of some mono- and poly-substituted purinesJournal of the Chemical Society, 1954
- Vitamin B12. X. 5,6-Dimethylbenzimidazole, a Degradation Product of Vitamin B12Journal of the American Chemical Society, 1950
- 552. Chemistry of the vitamin B12 group. Part I. Acid hydrolysis studies. Isolation of a phosphorus-containing degradation productJournal of the Chemical Society, 1950