Feeding of [3-¹³C, 2-¹⁵N]arginine, 38a, unequivocally established that the β-
arginine moiety of blasticidin S, 1, was formed from α-arginine by an intramolecular
migration of the α-amino group to the β- position. Further feedings using chirally
deuteriated arginines 38e and 38f revealed that the aminomutase process occurred with
inversion of...
The loss of all deuterium labels from previous feedings of [2-²H]-,
[3,3-²H₂]-, and [2,3,3-²H₃]arginines had indicated the possible intermediacy
of β-hydroxy- and β-ketoarginine (30 and 31, respectively) in the
biosynthesis of the streptolidine portion of streptothricin F (la).
In order to confirm or refute this evidence, D,L-[2,3,3,5,5-²H₅]-
arginine (32) was...
Two labelled arginines, DL-[2,3,3,-²H₃]arginine, 8,
and DL-[ ¹³C, 2-¹⁵N]arginine, 9, were synthesized. These
were fed to cultures of Streptomyces griseochromogenes in
order to probe the mechanism of the apparent arginine-2,3-
aminomutase reaction occurring in biosynthesis of blasticidin
S, 1. In previous studies of the enzymes lysine-2,3-
aminomutase and tyrosine-2,3-aminomutase different...