4. The structures shown below are related to the light-absorbing portion of green fluorescent proteins (GFPS),...
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4. The structures shown below are related to the light-absorbing portion of green fluorescent proteins (GFPS), originally isolated from marine organisms, including jellyfish, and widely used as reporter proteins in biochemical research. The (E) isomer converts to the (Z) form with a barrier of only about 13 kcal/mol, as compared to the barrier for a typical carbon-carbon pi bond of 65 kcal/mol. Two explanations for this lowered barrier have been proposed, as given in parts a and b below. For each part (a and b), show structures as appropriate to illustrate the explanations. Me Me energy barrier 13 kcal/mol Meo. N Meo Me N-Me (E) (2) O A "push-pull" resonance effect "in which a donating group...weakens the double bond a character". b. An addition/elimination mechanism involving a catalytic amount of a nucleophile. In one study, 4-dimethylaminopyridine (DMAP) was used. In a GFP system, a nucleophilic amino acid sidechain could play the catalytic-nucleophile role. Me Me N. used to catalyze the isomerization 4-dimethylaminopyridine (DMAP) 4. The structures shown below are related to the light-absorbing portion of green fluorescent proteins (GFPS), originally isolated from marine organisms, including jellyfish, and widely used as reporter proteins in biochemical research. The (E) isomer converts to the (Z) form with a barrier of only about 13 kcal/mol, as compared to the barrier for a typical carbon-carbon pi bond of 65 kcal/mol. Two explanations for this lowered barrier have been proposed, as given in parts a and b below. For each part (a and b), show structures as appropriate to illustrate the explanations. Me Me energy barrier 13 kcal/mol Meo. N Meo Me N-Me (E) (2) O A "push-pull" resonance effect "in which a donating group...weakens the double bond a character". b. An addition/elimination mechanism involving a catalytic amount of a nucleophile. In one study, 4-dimethylaminopyridine (DMAP) was used. In a GFP system, a nucleophilic amino acid sidechain could play the catalytic-nucleophile role. Me Me N. used to catalyze the isomerization 4-dimethylaminopyridine (DMAP)
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Organic Chemistry A Short Course
ISBN: 978-1111425562
13th edition
Authors: Harold Hart, Christopher M. Hadad, Leslie E. Craine, David J. Hart
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