Metabolism of L-α-arginine in the biosynthesis of blasticidin S Public Deposited

http://ir.library.oregonstate.edu/concern/graduate_thesis_or_dissertations/sn00b289n

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  • 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 mechanisms were demonstrated for each reaction. Our experiments were designed to reveal whether the mechanism of the arginine rearrangement is similar to either one of these or whether it is different from both. Blasticidin S obtained from each feeding was analyzed by high field NMR spectroscopy. We have found that an intramolecular migration of nitrogen from C-2 of α-arginine to C-3 of β- arginine takes place. In addition, our results indicate that when 8 was fed, at least some hydrogen migration from C-3 of α-arginine to C-2 of β-arginine had occurred. These results are qualitatively similar to those previously obtained for the lysine-2,3-aminomutase reaction.
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