Structural Elements of Methanopterin, a Novel Pterin

During short-time labeling experiments, cells of Methanobacterium thermoautotrophicum incorporate a substantial part of 14CO2 in a yellow fluorescent compound (called YFC) [Daniels, L. & Zeikus, J. G. (1978) J. Bacteriol. 136, 75-84]. As the compound was present only in small amounts, its more abundant, metabolic precursor was identified, extracted and purified by column chromatography. The chromophore of this compound is 2-amino-4-hydroxypteridine (pterin) as indicated by its ultraviolet-visible-light absorption and fluorescence properties. Decomposition studies revealed the presence of a number of structural elements, viz. glutamic acid, phosphate and a hexosamine. 1H-NMR and 13C-NMR spectra pointed to the presence of additional, as yet unidentified, elements. The compound is a complex, novel pterin derivative, which we have called methanopterin.