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

Article abstract of DOI:10.1021/ja00354a047

The formation of the β-lysine moiety of streptothricin F has been studied by feeding to Streptomyces L-1689-23 α-[3-¹³C,¹⁵N]-, α-[(3RS)-²H₂]-, α-[(3R)-²H]-, and α[(3S)-²H]lysine and β-[(2S)-²H]lysine. From the analysis of either the ¹³C NMR or ²H NMR spectrum of the derived antibiotics, it has been determined that the α-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 β-lysine indicates it is probably an intermediate in the biosynthesis of streptothricin F. The formation of the beta -lysine moiety of streptothricin F has been studied by feeding to Streptomyces L-1689-23 alpha - left bracket 3-**1**3C, **1**5N right bracket -, alpha - left bracket (3RS)-**2H//2 right bracket -, alpha - left bracket (3R)-**2H right bracket -, and alpha - left bracket (3S)-**2H right bracket lysine and beta - left bracket (2S)-**2H right bracket lysine. From the analysis of either the **1**3C NMR or **2H NMR spectrum of the derived antibotics, 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.