CHEM 313 Chapter : Chem_313_PS5_2014.pdf
Document Summary
Chem 313 problem set #5, 2014: the product on the right below is an important precursor in the shikimate pathway, which produces shikimic acid. It leads to an intermediate that is useful in the biosynthesis of a variety of metabolites. This precursor has been chemically prepared from the spontaneous rearrangement shown below (j. Ho: how do you explain that in basic aqueous solution (naoh, water), d-glucose rearrangement. You"ll find a mixture made of both aldoses in equilibrium with d-fructose. D-glucose: described the mechanism of the reaction depicted below catalyzed by oh-. Oh: based on your knowledge of aldol chemistry applied to carbohydrate, propose a mechanism for the conversion of glucose 6-phosphate to fructose 6-phosphate as catalyzed by phosphoglucose isomerase. Lys and his act as bases, but also their conjugated acids will give back the proton at some steps of the reaction. You can use the proton transfer short cut when appropriate.
