This Article Full Text (PDF) Alert me when this article is cited Alert me if a correction is posted Services Similar articles in this journal Similar articles in PubMed Alert me to new issues of the journal Download to citation manager Reprints and Permissions Copyright Information Books from ASM Press MicrobeWorld Citing Articles Citing Articles via HighWire Citing Articles via Google Scholar Google Scholar Articles by Reuke, B Articles by Bacher, A Search for Related Content PubMed PubMed Citation Articles by Reuke, B Articles by Bacher, A

research-article

Biosynthetic precursors of deazaflavins.

Lehrstuhl für Organische Chemie und Biochemie, Technische Universität München, Garching, Germany.

ABSTRACT

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.

This article has been cited by other articles:

• Isabelle, D., Simpson, D. R., Daniels, L. (2002). Large-Scale Production of Coenzyme F420-5,6 by Using Mycobacterium smegmatis. Appl. Environ. Microbiol. 68: 5750-5755 [Abstract] [Full Text]  
• Fischer, M., Romisch, W., Schiffmann, S., Kelly, M., Oschkinat, H., Steinbacher, S., Huber, R., Eisenreich, W., Richter, G., Bacher, A. (2002). Biosynthesis of Riboflavin in Archaea Studies on the Mechanism of 3,4-Dihydroxy-2-butanone-4-phosphate Synthase of Methanococcus jannaschii. J. Biol. Chem. 277: 41410-41416 [Abstract] [Full Text]  
• Choi, K.-P., Kendrick, N., Daniels, L. (2002). Demonstration that fbiC Is Required by Mycobacterium bovis BCG for Coenzyme F420 and FO Biosynthesis. J. Bacteriol. 184: 2420-2428 [Abstract] [Full Text]  
• Graupner, M., Xu, H., White, R. H. (2002). The Pyrimidine Nucleotide Reductase Step in Riboflavin and F420 Biosynthesis in Archaea Proceeds by the Eukaryotic Route to Riboflavin. J. Bacteriol. 184: 1952-1957 [Abstract] [Full Text]  
• Choi, K.-P., Bair, T. B., Bae, Y.-M., Daniels, L. (2001). Use of Transposon Tn5367 Mutagenesis and a Nitroimidazopyran-Based Selection System To Demonstrate a Requirement for fbiA and fbiB in Coenzyme F420 Biosynthesis by Mycobacterium bovis BCG. J. Bacteriol. 183: 7058-7066 [Abstract] [Full Text]