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...
Early studies on the biosynthesis of the quinoline quinone portion of
streptonigrin, 1, had suggested the intermediacy of novel aromatic amino
acids. In order to test this hypothesis, a series of compounds was synthesized
and tested for potential incorporation. [4-¹⁵N] 4-Aminoanthranilic acid,
4 5 a , [4-² H] 7-aminoquinaldinic acid,...
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...
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...
Early studies on the biosynthesis of Sarubicin A, 1, had suggested the
intermediacy of the novel aromatic amino acid 6-hydroxyanthranilic acid,
17. To investigate the biosynthetic steps beyond 17, [¹³C-¹⁵N carboxamide]
6-hydroxyanthranilamide, 27a, was synthesized, and fed to fermentations
of Streptomyces helicus. Incorporation of 27a into 1 provided suggestive
evidence...