The biosynthesis of the streptolidine moiety in streptothricin F

Article abstract of DOI:10.1016/S0040-4020(01)88659-2

A series of arginines specifically labeled either with ¹³C and ¹⁵N or with ²H were synthesized and fed to Streptomyces L-1689-23. The streptothricin F isolated in each case was analyzed by either ¹³C or ²H NMR, respectively, in order to determine the labeling pattern obtained. From these results, it appears that arginine is metabolized to a β-ketoarginine, possibly via a pyridoxal phosphate adduct, and then via cyclization, reduction, rearrangement, and hydroxylation to the streptolidine moiety. The pathway described can also account for the formation of other known antibiotics, and for β-hydroxy-γ-amino acids, generally.