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Streptonigrin Biosynthesis. 4. Details of the Tryptophan Metabolism

Gould, Steven J. and Chang, Chiu Chin and Darling, Dennis S. and Roberts, John D. and Squillacote, Michael (1980) Streptonigrin Biosynthesis. 4. Details of the Tryptophan Metabolism. Journal of the American Chemical Society, 102 (5). pp. 1707-1712. ISSN 0002-7863. doi:10.1021/ja00525a040. https://resolver.caltech.edu/CaltechAUTHORS:20151007-073140684

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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.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/ja00525a040DOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja00525a040PublisherArticle
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.
Funders:
Funding AgencyGrant Number
NSFCHE 76-05739
University of Connecticut Research FoundationUNSPECIFIED
NSFPCM 76-15197
U.S. Public Health Service (USPHS)GM-11072
Other Numbering System:
Other Numbering System NameOther Numbering System ID
Caltech Gates and Crellin Laboratories of Chemistry6171
Issue or Number:5
DOI:10.1021/ja00525a040
Record Number:CaltechAUTHORS:20151007-073140684
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20151007-073140684
Official Citation:Streptonigrin biosynthesis. 4. Details of the tryptophan metabolism Steven J. Gould, Chiu Chin Chang, Dennis S. Darling, John D. Roberts, and Michael Squillacote Journal of the American Chemical Society 1980 102 (5), 1707-1712 DOI: 10.1021/ja00525a040
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:60833
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:07 Oct 2015 16:14
Last Modified:10 Nov 2021 22:40

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