On the Mechanism of the Conversion of Dethiobiotin to Biotin in E. coli. Studies with Deuterated Precursors Using Tandem Mass Spectroscopic (MS-MS) Techniques

Article abstract of DOI:10.1021/jo00133a004

The last step of the biosynthesis of biotin (1), i.e., the conversion of dethiobiotin (2) into biotin has been studied in E.Coli by starting from specifically deuterated precursors: <3-(2)H_0;1,4-(2)H_1;0>-, <5,5,5-(2)H₃>-, and <6,6-(2)H₂>-dl-dethiobiotins.Deuterium has been localized in the biosynthesized biotin by using MS-MS techniques.In each case, it is possible to conclude to the absence of deuterium migration: the two C-S bonds of biotin are formed with removal of only one hydrogen from C-2 and C-5 and without involvement of the adjacent positions.