title: Structures of coenzyme F(420) in Mycobacterium species.
abstract: The structure of coenzyme F(420) in Mycobacterium smegmatis was examined using proton NMR, amino acid analysis, and HPLC. The two major F(420) structures were shown to be composed of a chromophore identical to that of F(420) from Methanobacterium thermoautotrophicum, with a side chain of a ribityl residue, a lactyl residue and five or six glutamate groups (F(420)-5 and F(420)-6). Peptidase treatment studies suggested that L-glutamate groups are linked by gamma-glutamyl bonds in the side chain. HPLC analysis indicated that Mycobacterium tuberculosis, Mycobacterium bovis BCG, and Mycobacterium fortuitum have F(420)-5 and F(420)-6 as the predominant structures, whereas Mycobacterium avium contains F(420)-5, F(420)-6 and F(420)-7 in significant amounts. 7,8-Didemethyl 8-hydroxy 5-deazariboflavin (FO), an intermediate in F(420) biosynthesis, accounted for about 1-7% of the total deazaflavin in cells. Peptidase treatment of F(420) created F(420) derivatives that may be useful for the assay of enzymes involved in F(420) biosynthesis.
authors.affiliation: Department of Microbiology, University of Iowa, Iowa City, Iowa 52242, USA.
authors.forename: T B
authors.initials: TB
authors.lastname: Bair
authors.forename: D W
authors.initials: DW
authors.lastname: Isabelle
authors.forename: L
authors.initials: L
authors.lastname: Daniels
mesh_terms: D000596:Amino Acids / Q000032:analysis; D002384:Catalysis; D002851:Chromatography, High Pressure Liquid; D019605:Euryarchaeota / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D009161:Mycobacterium / Q000737:chemistry*; D010447:Peptide Hydrolases / Q000378:metabolism; D012256:Riboflavin / Q000031:analogs & derivatives* / Q000737:chemistry* / Q000302:isolation & purification / Q000378:metabolism
chemical_list: D000596:Amino Acids; C015084:coenzyme F420; D010447:Peptide Hydrolases; D012256:Riboflavin