Erickson, W. R. ; Gould, S. J. "Streptonigrin Biosynthesis 8. Evidence for The Involvement of a New Shikimate Pathway Product and a New Route to Quinolines." J. Am. Chem. Soc. 1987, 109, 620.

Abstract:  Streptonigrin (I) exchanged oxygen with water exclusively at the C-8 carbonyl. [4 15N]4 aminoanthrilic acid and [4-2H]7-aminoquinoline-2-carboxylic acid were synthesized, and, when fed to fermns. of Streptomyces flocculus, were incorporated into I. Evidently, 4-aminoanthranilic acid is a new product of the shikimate pathway. This may be a fundamentally new route for the biol. formation of quinoline rings.

Erickson, W. R. ; Gould, S. J. "Streptonigrin Biosynthesis 7. Incorporation of Oxygen from 18O2: Evidence for an Oxidative ß-Carboline Cleavage." J. Am. Chem. Soc. 1985, 107, 5831.

Abstract: Fermentation of Streptomyces flocculus in the presence of 18O2 resulted in the prodn. of streptonigrin (I) and the incorporation of 18O at 5 positions: at C-8', -9', and -10' of the Ph ring and at C-5 and -6 of the quinone ring. Thus, the oxygenation and cleavage of the b-carboline biosynthetic intermediate are all oxidative processes. Also, 4-amino-3-hydroxyanthranilic acid may be the precursor of the quinone ring.

Erickson, W. R. "Studies On Advanced Intermediates In The Biosynthesis Of Streptonigrin"

Abstract:  Ph. D. Dissertation, Oregon State University, 1987.