2. As you are probably aware, some proteins "glow," most famously Green Fluorescent Protein (2008 Nobel Prize in Chemistry). The color of these proteins can be shifted by an elimination reaction as described in the article "The E1 Mechanism in Photo-Induced ß-Elimination Reactions for Green-to-Red Conversion of Fluorescent Proteins."

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Chapter11: Chemical Kinetics
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Problem 11.49PAE: The rate of photodecomposition of the herbicide piclo- ram in aqueous systems was determined by...
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2. As you are probably aware, some proteins "glow," most famously Green Fluorescent Protein
(2008 Nobel Prize in Chemistry). The color of these proteins can be shifted by an elimination
reaction as described in the article "The E1 Mechanism in Photo-Induced B-Elimination
Reactions for Green-to-Red Conversion of Fluorescent Proteins."
NRVF.
NRVF.
His-Nu H
N-ATTL.
KİKGRX
ATTL.
HO
NH
HO
His-Ce
hv
His-CB
a) Propose a simple mechanism for the reaction using arrow pushing.
b) How might His-Na (which sits in the surrounding protein) accelerate the reaction? To initiate
the reaction, should this histidine be in its acid or conjugate base form? Draw this form of
histidine side chain.
c) How about His-CB?
d) Provide a brief explanation of why the reaction yields a shift from green to red color.
Transcribed Image Text:2. As you are probably aware, some proteins "glow," most famously Green Fluorescent Protein (2008 Nobel Prize in Chemistry). The color of these proteins can be shifted by an elimination reaction as described in the article "The E1 Mechanism in Photo-Induced B-Elimination Reactions for Green-to-Red Conversion of Fluorescent Proteins." NRVF. NRVF. His-Nu H N-ATTL. KİKGRX ATTL. HO NH HO His-Ce hv His-CB a) Propose a simple mechanism for the reaction using arrow pushing. b) How might His-Na (which sits in the surrounding protein) accelerate the reaction? To initiate the reaction, should this histidine be in its acid or conjugate base form? Draw this form of histidine side chain. c) How about His-CB? d) Provide a brief explanation of why the reaction yields a shift from green to red color.
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