Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)

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van Beelen, P. et al.

Derivatives of methanopterin, a coenzyme involved in methanogenesis.

Degradational studies of methanopterin, a coenzyme involved in methanogenesis, are reported. The results of these studies are in full accordance with the proposed structure of methanopterin as N-[1'-(2''-amino-4''-hydroxy-7'' -methyl-6''-pteridinyl)ethyl]-4-[2', 3', 4', 5'-tetrahydroxypent-1'-yl(5'-1'' )O-alpha-ribofuranosyl-5''-phosphoric acid] aniline in which the phosphate group is esterified with alpha-hydroxyglutaric acid. Acid hydrolysis of methanopterin cleaved the 5'----1'' glycosidic bond and yielded a 'hydrolytic product' which was identified as N-[1'-(2''-amino-4''-hydroxy-7'' -methyl-6''-pteridinyl)ethyl]-4-[2', 3', 4', 5'-tetrahydroxypent-1'-yl]aniline. Alkaline permanganate oxidation of methanopterin yielded 7-methylpterin-6-carboxylic acid. Catalytic (or enzymatic) hydrogenation of methanopterin gave a mixture of 6-ethyl-7-methyl-7,8-dihydropterin, 6-ethyl-7-methylpterin and a third compound, named methaniline which was identified as 4-[2', 3', 4', 5'-tetrahydroxypent-1'-yl(5'----1'')O-alpha -ribofuranosyl-5''-phosphoric acid]aniline, in which the phosphate group is esterified with alpha-hydroxyglutaric acid. Methanosarcina barkeri contains a closely related coenzyme called sarcinapterin, which was identified as a L-glutamyl derivative of methanopterin, where the glutamate moiety is attached to the alpha-carboxylic acid group of the alpha-hydroxyglutaric acid moiety of methanopterin via an amide linkage.[1]

References

Derivatives of methanopterin, a coenzyme involved in methanogenesis. van Beelen, P., Labro, J.F., Keltjens, J.T., Geerts, W.J., Vogels, G.D., Laarhoven, W.H., Guijt, W., Haasnoot, C.A. Eur. J. Biochem. (1984) [Pubmed]

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