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The Biosynthesis of the Triterpene, Eburicoic Acid: The Utilization of Methyl-labeled Acetate

Dauben, William G. and Ban, Yoshio and Richards, John H. (1957) The Biosynthesis of the Triterpene, Eburicoic Acid: The Utilization of Methyl-labeled Acetate. Journal of the American Chemical Society, 79 (4). pp. 968-970. ISSN 0002-7863. http://resolver.caltech.edu/CaltechAUTHORS:20150428-125502290

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Abstract

The C_(31)-triterpene, eburicoic acid, has been biosynthesized by allowing P. sulfureus to grow on a medium containing methyl-labeled acetate. By degradation of the acid, it has been shown that the carboxyl carbon, C_(21), and the two methyl groups, C_(30) and C_(31), of the gem-dimethyl group of ring A are derived from the methyl of acetate. Such a distribution is predicted on the basis of the squalene hypothesis of a "universal" biosynthetic mechanism leading to both the triterpenes and the sterols. It also was found that the extra carbon atom, C_(28), found on C_(24) of the side-chain is not derived from acetate.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/ja01561a052DOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja01561a052PublisherArticle
Additional Information:© 1957 American Chemical Society. Received July 16, 1956. This work was supported, in part, by grant No. AT(11-1)-34, Project No. 16, U.S. Atomic Energy Commission. [JRH] National Science Foundation Predoctoral Fellow, 1954-1955.
Funders:
Funding AgencyGrant Number
Atomic Energy CommissionAT(11-1)-34
NSF Predoctoral FellowshipUNSPECIFIED
Record Number:CaltechAUTHORS:20150428-125502290
Persistent URL:http://resolver.caltech.edu/CaltechAUTHORS:20150428-125502290
Official Citation:The Biosynthesis of the Triterpene, Eburicoic Acid: The Utilization of Methyl-labeled Acetate William G. Dauben, Yoshio Ban, and John H. Richards Journal of the American Chemical Society 1957 79 (4), 968-970 DOI: 10.1021/ja01561a052
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:57050
Collection:CaltechAUTHORS
Deposited By: George Porter
Deposited On:28 Apr 2015 20:10
Last Modified:13 Feb 2019 18:03

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