Biosynthesis of streptothricin F. 5. Formation of .beta.-lysine by Streptomyces L-1689-23

The formation of the beta -lysine moiety of streptothricin F has been studied by feeding to Streptomyces L-1689-23 alpha -(3- super(13)C, super(15)N)-, alpha ((3RS)- super(2)H sub(2))-, alpha -((3R)- super(2)H)lysine and beta -((2S)- super(2)H)lysine. From the analysis of either the super(13)C NMR or super(2)H NMR spectrum of the derived antibiotics, it has been determined that the alpha -nitrogen migrates to C-3 with inversion of configuration by an intramolecular process, and the 3-pro-R hydrogen migrates to C-2 with inversion of configuration by a process that is substantially or completely intermolecular. The very high degree of incorporation of labeled beta -lysine indicates it is probably an intermediate in the biosynthesis of streptothricin F.