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Nuclear Magnetic Resonance Spectroscopy. Carbon-13 Spectra of Some Macrolide Antibiotics and Derivatives. Substituent and Conformational Effects

Nourse, James G. and Roberts, John D. (1975) Nuclear Magnetic Resonance Spectroscopy. Carbon-13 Spectra of Some Macrolide Antibiotics and Derivatives. Substituent and Conformational Effects. Journal of the American Chemical Society, 97 (16). pp. 4584-4594. ISSN 0002-7863. http://resolver.caltech.edu/CaltechAUTHORS:20151008-153159079

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Abstract

Carbon-13(^(13)C NMR) chemical shifts are reported and assigned for a series of naturally occurring macrolide antibiotics, biosynthetic precursors, shunt metabolites, and derivatives. Besides the usual ^(13)C NMR substituent effects, the results are interpreted with reference to conformational models proposed for these compounds. A number of proposals are made concerning the conformations of the various derivatives, the differences between them, and the possibility of internal motion. The usefulness of ^(13)C NMR in ascertaining hydrogen bonding and in the structural analysis of these important cornpounds is demonstrated.


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http://dx.doi.org/10.1021/ja00849a021DOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja00849a021PublisherArticle
Additional Information:© 1975 American Chemical Society. Received October 4, 1974. We are grateful to Dr. Richard S. Egan, Dr. James B. McAlpine. and the staff of Abbott Laboratories for the generous donation of most of the samples used in this study, for the use of extensive unpublished data. and for stimulating discussions and correspondence. Supported by the Public Health Service. Research Grant No. GM-11072, from the Division of General Medical Sciences, and by the National Science Foundation. National Institutes of Health Trainee, 1970- 1973.
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Funding AgencyGrant Number
Abbott LaboratoriesUNSPECIFIED
U.S. Public Health Service (USPHS)GM-11072
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Caltech Gates and Crellin Laboratories of Chemistry4975
Record Number:CaltechAUTHORS:20151008-153159079
Persistent URL:http://resolver.caltech.edu/CaltechAUTHORS:20151008-153159079
Official Citation:Nuclear magnetic resonance spectroscopy. Carbon-13 spectra of some macrolide antibiotics and derivatives. Substituent and conformational effects James G. Nourse and John D. Roberts Journal of the American Chemical Society 1975 97 (16), 4584-4594 DOI: 10.1021/ja00849a021
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:60923
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:10 Oct 2015 12:09
Last Modified:10 Oct 2015 12:09

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