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The Biosynthesis of the Triterpene, Eburicoic Acid

Dauben, William G. and Richards, John H. (1956) The Biosynthesis of the Triterpene, Eburicoic Acid. Journal of the American Chemical Society, 78 (20). pp. 5329-5335. ISSN 0002-7863. doi:10.1021/ja01601a047.

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The C_(31) triterpene, eburicoic acid, has been biosynthesized by allowing P. sulfureus to grow on a medium containing carboxyl-labeled acetate. Labeled eburicoic acid has been obtained and by stepwise degradation of the molecule the following facts have been established: (a) the acetate is utilized as a two carbon unit, (b) C_4 of ring A and C_(11) and C_(12) of ring C are labeled, and (c) the gem-dimethyl group, C_(30) and C_(31), of ring A, the carboxyl group, C_(21), and the extra methylene carbon atom, C_(28), in the side-chain are not labeled. The specific activities of the labeled carbon atoms are those expected for an eburicoic acid molecule containing 12 carbon atoms derived from the carboxyl of acetate. The location of the labeled atoms and their specific activities are those predicted on the basis of the squalene hypothesis as the mechanism of biosynthesis for steroids and triterpenes. Of particular interest is the demonstration that both C_(11) and C_(12) are derived from the carboxyl carbon of acetate since such is a necessary requirement if squalene is to be utilized as an intact molecule.

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Additional Information:© 1956 American Chemical Society. Received May 7, 1956. A preliminary announcement of a portion of this work appeared in Chemistry & industry, 94 (1955). 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. We wish to thank Mr. J. L. Somerville of the Australian Newsprint Mills, Boyer, Tasmania, for kindly supplying the eburicoic acid, Professor H. H. Hansen and Professor E. A. Adelberg of the University of California for their assistance in the early growth experiments and Dr. E. M. Baker of the Radiation Laboratory, University of California, for the determination of activity in the C_(28) determination.
Funding AgencyGrant Number
Atomic Energy CommissionAT(11-1)-34
NSF Predoctoral FellowshipUNSPECIFIED
Issue or Number:20
Record Number:CaltechAUTHORS:20150428-124150243
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Official Citation:The Biosynthesis of the Triterpene, Eburicoic Acid William G. Dauben and John H. Richards Journal of the American Chemical Society 1956 78 (20), 5329-5335 DOI: 10.1021/ja01601a047
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:57048
Deposited By: George Porter
Deposited On:28 Apr 2015 19:58
Last Modified:10 Nov 2021 21:07

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