Structural characterization of tatiopterin, a novel pterin isolated from Methanogenium tationis.
Cofactor extracts of Methanogenium tationis were screened for the presence of pterin-derivatives. Methanopterin, sarcinapterin and 7-methylpterin were absent, while 2-amino-4-hydroxy-pteridine and another blue fluorescent compound with a pterin spectrum were detected. The latter pterin was purified by ion exchange and reversed-phase column chromatography. The structure of this compound was elucidated by combining spectrophotometry, amino acid analysis and 1H-NMR spectroscopy. The pterin, which we named tatiopterin, was identified as an aspartyl derivative of sarcinapterin with a 7-proton instead of a 7-methyl group in the pterin moiety. The IUPAC name is: N-[-1'-(2''-amino-4''-hydroxy-7''-proton-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-hydroxyglutarylglutamylaspartic acid.
Raemakers-Franken
P C
PC
Department of Microbiology, Faculty of Science, University of Nijmegen, The Netherlands.
Voncken
F G
FG
Korteland
J
J
Keltjens
J T
JT
van der Drift
C
C
Vogels
G D
GD
D000596:Amino Acids / Q000032:analysis; D019605:Euryarchaeota / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy; D011622:Pterins / Q000032:analysis*; D012256:Riboflavin / Q000031:analogs & derivatives / Q000378:metabolism; D013050:Spectrometry, Fluorescence; D013056:Spectrophotometry, Ultraviolet
D000596:Amino Acids; D011622:Pterins; C062888:tatiopterin; C015084:coenzyme F420; D012256:Riboflavin