Formation of Roseoflavin from 8-Amino- and 8-Methylamino-8-Demethyl-D-Riboflavin

• Published in: Journal of biochemistry (Tokyo) Vol. 101; no. 3; pp. 705 - 711
• Main Authors: JURI, Natsuyo, KUBO, Yoko, KASAI, Sabu, OTANI, Shohei, KUSUNOSE, Masamichi, MATSUI, Kunio
• Format: Journal Article
• Language: English
• Published: Oxford Oxford University Press 01.03.1987
• Subjects: Bacteriology; Biological and medical sciences; Chromatography, Thin Layer; Fundamental and applied biological sciences. Psychology; Metabolism. Enzymes; Methionine; Microbiology; Riboflavin - analogs & derivatives; Riboflavin - biosynthesis; Riboflavin - metabolism; Streptomyces - metabolism; Actinomycetales; Flavin derivatives; Streptomycetaceae; Chemical structure; Pigments; Riboflavin; Streptomyces; Bacteria; Actinomycetes; Biosynthesis; Antimicrobial agent; Chromatography
• DOI: 10.1093/jb/101.3.705
• ISSN: 0021-924X

A synthesis of roseoflavin (RoF) by Streptomyces davawensis from 8-amino- (AF) and 8-methylamino-8-demethyl-D-riboflavin (MAF) was demonstrated. The lines of evidence are: 1) the RoF formation was increased by addition of AF or MAF to the culture, 2) [2-14C]RoF was formed by addition of [2-14C]AF or [2-14C]MAF to the culture, and the location of the 14C atom at the 2-position was demonstrated by identifying [14C]urea in the hydrolysate of the RoF, 3) [N-methyl-14C]RoF was formed by addition of [methyl-14C]methionine to the culture containing AF or MAF, and the location of the 14C atom was confirmed by the photochemical conversion of the RoF to MAF, the specific radioactivity of which was about half that of the original RoF, and by localization of the 14C atom in 1,2-dihydro-6-methyl-7-dimethyl-amino-2-keto-1-ribityl-3-quinoxalinecarboxylic acid (QC), which was formed from the RoF by hydrolysis.