Reinvestigation of compound X, a suspected biotin intermediate: identification of N-formyl derivatives of biotin and dethiobiotin.
Compound X, reported as an intermediate in the biosynthesis of biotin from dethiobiotin (DTB) (Biochem. Biophys. Res. Commun., 88, 312 (1979)), was found to contain N-formyl DTB and biotin. The methyl ester of N-formyl biotin was considered to be a product from the biotin, which was biosynthesized from DTB by resting cells of E. coli C 124, through treatment with diazomethane in the presence of a trace amount of formic acid after Dowex 1X2 column chromatography. NMR analysis revealed that biotin was formylated at 1'-N. N-Formylated DTB and biotin are new biotin derivatives.
D001710:Biotin / Q000031:analogs & derivatives* / Q000378:metabolism; D002852:Chromatography, Ion Exchange; D003978:Diazomethane; D004926:Escherichia coli / Q000032:analysis*
D003978:Diazomethane; D001710:Biotin; C004749:desthiobiotin