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United States Department of Agriculture

Agricultural Research Service

Title: Preparation of Two Stereochemically Defined Isomers of Deuterium Labeled Delta-Cadinene

Authors
item Stipanovic, Robert
item Williams, Howard - TEXAS A&M UNIVERSITY
item Sattler, Isabel - TEXAS A&M UNIVERSITY
item Scott, A - TEXAS A&M UNIVERSITY
item Vinson, S - TEXAS A&M UNIVERSITY
item Liu, Jinggao - TEXAS A&M UNIVERSITY

Submitted to: Journal of Labelled Compounds and Radiopharmaceuticals
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: October 8, 1996
Publication Date: N/A

Interpretive Summary: Antibiotic compounds produced by cotton when it is infected with wilt pathogens are essential elements in the plant's resistance mechanism. In order to increase resistance, it is important to understand the biosynthesis of these compounds. Others have proposed that delta-cadinene is the biosynthetic precursor to these antibiotics in cotton. We have synthesized two delta-cadinenes which are stereospecifically labeled with deuterium. Use of this compound in feeding studies in cell free extracts of cotton will allow us to prove this hypothesis and investigate the stereospecific loss of hydrogen during the synthesis of these compounds.

Technical Abstract: Deuterated delta-cadinene needed for biosynthetic feeding studies in cotton was prepared by acid catalyzed rearrangements of (-)-alpha-cubebene and (+, -)-alpha-copaene. In both cases, one deuterium was incorporated in the 7 position. Stereochemistry of the added deuterium was determined by 1H NMR spectroscopy to be exclusively cis to the isopropyl group in the alpha-copaene derived product and predominantly trans (20% cis) to the isopropyl group in the cubebene derived product.

Last Modified: 9/20/2014
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