Abstract
Growing cultures of Methanobacterium thermoautotrophicum were supplemented with [U-14C]adenosine or [1′-14C]adenosine. 7,8-Didemethyl-8-hydroxy-5-deazariboflavin (factor F0) and 7-methylpterin were isolated from the culture medium. Hydrolysis of cellular RNA yielded purine and pyrimidine nucleotides. The ribose side chain of proffered adenosine is efficiently incorporated into cellular adenosine and guanosine nucleotide pools but not into pyrimidine nucleotides. Thus, M. thermoautotrophicum can utilize exogenous adenosine by direct phosphorylation without hydrolysis of the glycosidic bond, and AMP can be efficiently converted to GMP. Factor F0 and 7-methylpterin had approximately the same specific activities as the purine nucleotides. It follows that the ribityl side chain of factor F0 is derived from the ribose side chain of a nucleotide precursor by reduction. The pyrazine ring of methanopterin is formed by ring expansion involving the ribose side chain of the precursor, GTP.
This is a preview of subscription content, log in via an institution to check access.
Abbreviations
- Factor F0 :
-
8-hydroxy-6,7-didemethyl-5-deazariboflavin
- APRT:
-
adenine phosphoribosyltransferase
- GPRT:
-
guanine phosphoribosyltransferase
- PRPP:
-
phosphoribosylpyrophosphate
- HPLC:
-
high performance liquid chromatography
References
Bacher A (1990) Biosynthesis of riboflavin. In: Müller F (ed) Chemistry and biochemistry of flavins. Chemical Rubber Company, Cleveland (in press)
Bacher A, Volk R, Keller PJ, Floss HG, Le Van Q, Eisenreich W, Schwarzhopf B (1987) Biosynthesis of flavins and deazaflavins. In: Edmondson DE, McCormick DB (eds) Flavins and flavoproteins. Walter de Gruyter, Berlin, pp 431–440
Brown GM, Williamson RD (1987) Biosynthesis of folic acid, riboflavin, thiamine, and pantothenic acid. In: Neidhardt FC (ed) Escherichia coli and Salmonella typhinurium. Cellular and molecular biology, vol 1. American Society for Microbiology, Washington, pp 521–538
Burrows RB, Brown GM (1978) Presence in Escherichia coli of deaminase and a reductase involved in biosynthesis of riboflavin. J Bacteriol 136: 657–667
Eirich LD, Vogels GD, Wolfe RS (1978) Proposed structure for coenzyme F420 from Methanobacterium. Biochemistry 17: 4583–4593
Foor F, Brown GM (1975) Purification and properties of guanosine triphosphate cyclohydrolase II from Escherichia coli. J Biol Chem 250: 3545–3551
Hauska G (1988) Elucidation of methanogenesis seems well on its way. Trends Biochem Sci 13: 2–4
Hochstadt J (1978) Adenine phosphoribosyltransferase from Escherichia coli. Meth Enzymol 51: 558–567
Hove-Jensen B, Harlow KW, King CJ, Switzer RL (1986) Phosphoribosylpyrophosphate synthetase of Escherichia coli. J Biol Chem 261: 6765–6771
Jaenchen R, Schönheit P, Thauer RK (1984) Studies on the biosynthesis of coenzyme F420 in methanogenic bacteria. Arch Microbiol 137: 362–365
Keller PJ, Floss HG, Le Van Q, Schwarzkopf B, Bacher A (1986) Biosynthesis of methanopterin in Methanobacterium thermoautotrophicum. J Am Chem Soc 108: 344–345
Kiener A, Holliger C, Leisinger T (1984) Analogue-resistant and auxotrophic mutants of Methanobacterium thermoautotrophicum. Arch Microbiol 139: 87–90
Le Van Q, Schwarzkopf B, Bacher A, Keller PJ, Lee S, Floss HG (1985) Biosynthesis of 7,8-didemethyl-8-hydroxy-5-deazariboflavin, the chromophoric moiety of coenzyme F420. J Am Chem Soc 107: 8300–8301
Luria SE, Burrous JW (1957) Hybridization between Escherichia coli and Shigella. J Bacteriol 74: 461–476
Mailänder B, Bacher A (1976) Biosynthesis of riboflavin. J Biol Chem 251: 3623–3628
Scherer P, Höllriegel V, Krug C, Bokel M, Renz P (1984) On the biosynthesis of 5-hydroxybenzimidazolylcobamide (vitamin B12-factor III) in Methanosarcina barkeri. Arch Microbiol 138: 354–359
Van Beelen P, Labro JFA, Keltjens JT, Geerts WJ, Vogels GD, Laarhoven WH, Guijt W, Haasnoot CAG (1984) Derivatives of methanopterin, a coenzyme involved in methanogenesis. Eur J Biochem 139: 359–365
Volk R, Bacher A (1988) Biosynthesis of riboflavin. The structure of the purine precursor. J Am Chem Soc 110: 3651–3653
White RH (1985a) Biosynthesis of 5-(p-aminophenyl)-1,2,3,4-tetrahydroxypentane by methanogenic bacteria. Arch Microbiol 143: 1–5
White RH (1985b) 7-Methylpterin and 7-methyllumazine: Oxidative degradation products of 7-methyl-substituted pteridines in methanogenic bacteria. J Bacteriol 162: 516–520
White RH (1986) Biosynthesis of the 7-methylated pterin of methanopterin. J Bacteriol 165: 215–218
Wolfe RS (1985) Unusual coenzymes of methanogenesis. Trends Biochem Sci 10: 396–399
Yim JJ, Brown GM (1976) Characteristics of guanosine triphosphate cyclohydrolase I purified from Escherichia coli. J Biol Chem 251: 5087–5094
Zeikus JG, Wolfe RS (1972) Methanobacterium thermoautotrophicum sp. n., an anacrobic, autotrophic, extreme thermophile. J Bacteriol 109: 707–713
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Schwarzkopf, B., Reuke, B., Kiener, A. et al. Biosynthesis of coenzyme F420 and methanopterin in Methanobacterium thermoautotrophicum . Arch. Microbiol. 153, 259–263 (1990). https://doi.org/10.1007/BF00249078
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF00249078