Biosynthetic precursors of deazaflavins.
The incorporation of 13C- and 14C-labeled precursors into 5-deaza-7,8-didemethyl-8-hydroxyriboflavin (factor F0) was studied with growing cells of Methanobacterium thermoautotrophicum. 5-Amino-6-ribitylamino-2,4(1H,3H)-pyrimidinedione was incorporated into the deazaflavin and into riboflavin without dilution. Tyrosine and 4-hydroxyphenylpyruvate were incorporated into the deazaflavin and into cellular protein. 4-Hydroxybenzaldehyde was not incorporated. A reaction mechanism is proposed for the formation of the deazaflavin chromophore from 5-amino-6-ribitylamino-2,4(1H,3H)-pyrimidinedione and tyrosine or 4-hydroxyphenylpyruvate.
Lehrstuhl für Organische Chemie und Biochemie, Technische Universität München, Garching, Germany.
B
B
Reuke
S
S
Korn
W
W
Eisenreich
A
A
Bacher
D005415:Flavins / Q000096:biosynthesis*; D009682:Magnetic Resonance Spectroscopy; D017014:Methanobacterium / Q000378:metabolism*; D010667:Phenylpyruvic Acids / Q000378:metabolism; D012256:Riboflavin / Q000096:biosynthesis; D014443:Tyrosine / Q000096:biosynthesis / Q000378:metabolism; D014444:Tyrosine Transaminase / Q000302:isolation & purification / Q000378:metabolism; D014529:Uridine / Q000031:analogs & derivatives / Q000378:metabolism
D005415:Flavins; D010667:Phenylpyruvic Acids; C010590:4-hydroxyphenylpyruvic acid; C040523:5-amino-6-ribitylamino-2,4-(1H,3H)pyrimidinedione; C019319:5-deazaflavin; D014443:Tyrosine; D014444:Tyrosine Transaminase; D012256:Riboflavin; D014529:Uridine