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Published February 27, 1980 | public
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Streptonigrin Biosynthesis. 4. Details of the Tryptophan Metabolism

Gould, Steven J.
Chang, Chiu Chin
Darling, Dennis S.
Roberts, John D.
Squillacote, Michael
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Abstract

Details of the metabolism of tryptophan leading to the biosynthesis of streptonigrin have been elucidated. These include identification of L-tryptophan as the natural precursor, the isolation of an early intermediate in the pathway, and the use of ^(15)N-^(13)C heteronuclear spin couplings to eludicate the N-C bond cleavage leading to the 4-phenylpicolinic acid portion (C-D rings). Additional feedings have apparently eliminated the possible involvement of all known pathways leading to quinoline rings; suggestions for the origin of this portion (A-B rings) are presented.

Additional Information

© 1980 American Chemical Society. Received July 23, 1979. We are indebted to Dr. John DeZeeuw of Pfizer and Co., Inc., Croton, Conn., for strains of S.flocculus and to Dr. John Douros of Drug Research and Development, Chemotherapy, NCI, for generous gifts of streptonigrin. Professor Edward Samulski and Dr. Thomas Leipert of the Department of Chemistry, University of Connecticut, are thanked for obtaining the ^(13)C NMR spectra; the Bruker WP-90 spectrometer used for this was purchased in part by a grant from the National Science Foundation (CHE 76-05739). Dr. James Stuart of the Department of Chemistry, University of Connecticut, is thanked for advice and help with the LC analysis of the β-methyltryptophans. This work was supported in part by grants from the University of Connecticut Research Foundation and the National Science Foundation (PCM 76-15197) to S.J.G. and Public Health Service Grant GM-11072 from the Division of General Medical Sciences to J.D.R.

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