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Title:Investigation of the Stereochemistry of the Methyl-to-Methylene Elimination in the Biosynthesis of Several Terpenes Through the Use of Chiral Methyl Labeled Compounds
Author(s):Elmore, Charles Sherman
Doctoral Committee Chair(s):Coates, R.M.
Department / Program:Chemistry
Discipline:Chemistry
Degree Granting Institution:University of Illinois at Urbana-Champaign
Degree:Ph.D.
Genre:Dissertation
Subject(s):Chemistry, Biochemistry
Abstract:The synthesis of (R)- (13-$\sp2$H, $\sp3$H) farnesyl diphosphate has been completed by methodology similar to that used for the synthesis of (R)- (9-$\sp2$H, $\sp3$H) geranyl diphosphate. Incubation of the radiolabeled farnesyl diphosphate with 5-epi-aristolochene synthase gave the ($\sp2$H, $\sp3$H) olefin in a 10% radiochemical yield. Analysis by $\sp3$H NMR spectroscopy showed 3 peaks in a 5:1:0.7 ratio which correspond to the (12-$\sp2$H, $\sp3$H) -, (12-$\sp1$H, $\sp3$H) -, and (1-$\sp3$H, 12-$\sp2$H) 5-epi-aristolochene, respectively. However, the assignment of these peaks and the determination of the facial selectivity of the enzyme were not possible owing to the lack of a reference sample of 5-epi-aristolochene for NMR comparisons and NOE experiments.
Issue Date:1997
Type:Text
Language:English
Description:171 p.
Thesis (Ph.D.)--University of Illinois at Urbana-Champaign, 1997.
URI:http://hdl.handle.net/2142/84376
Other Identifier(s):(MiAaPQ)AAI9812580
Date Available in IDEALS:2015-09-25
Date Deposited:1997


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