The plant toxin fluoroacetate (F-CH2COO2) is easily converted to fluorocitrate when an animal ingests the plant. The2-fluoro-3-hydroxy citrate molecule is a suicide substrate forthe enzyme aconitase. Consider the overall goal of thisenzyme (to remove the OH group from the tertiary carbonand place another OH group on a secondary carbon) andspeculate as to why the reaction to produce isocitrate does notoccur as planned. (Hint: Fluorine is more electronegativethan oxygen.)

Biochemistry
6th Edition
ISBN:9781305577206
Author:Reginald H. Garrett, Charles M. Grisham
Publisher:Reginald H. Garrett, Charles M. Grisham
Chapter18: Glycolysis
Section: Chapter Questions
Problem 24P: Based on your knowledge of the structure of NAD+ and an assumption that coenzyme dissociation is the...
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The plant toxin fluoroacetate (F-CH2
COO2) is easily converted to fluorocitrate when an animal ingests the plant. The
2-fluoro-3-hydroxy citrate molecule is a suicide substrate for
the enzyme aconitase. Consider the overall goal of this
enzyme (to remove the OH group from the tertiary carbon
and place another OH group on a secondary carbon) and
speculate as to why the reaction to produce isocitrate does not
occur as planned. (Hint: Fluorine is more electronegative
than oxygen.)

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