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Chem+135+Spring+2010+-+Problem+Set+4+-+Answer+Key - CHEM...

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CHEM 135 Spring 2010 Problem Set 4 Due Thursday, March 11 at the beginning of class 1. An area of significant interest is the production of industrial feedstock chemicals through biofermentation processes. In one example, two molecules of pyruvate can be enzymatically converted to acetolactate, which is carried on by acetoin synthase to produce acetoin. The acetoin is then collected and converted to butadiene (a building block for synthetic rubber-like polymers) through a series of non-biological transformations. a. The first step in this process is catalyzed by acetolactate synthase, which is a TPP- dependent enzyme. Provide a clear arrow-pushing mechanism for this reaction. You do not have to provide the full structure of the cofactor – just supply the portion that is required for mechanistic steps. b. Provide a reasonable arrow-pushing mechanism for the step that is catalyzed by acetoin synthase. 2. You have discovered a new species of plant that can synthesize glucose using aspartic acid as a starting material. The first part of this pathway involves two enzymatic steps that convert aspartate to phosphoenol pyruvate (PEP). The first reaction, which requires the reduction of NADP + to NADPH, results in the formation of intermediate X and NH 4 . The second reaction, which requires the hydrolysis of GTP (an ATP analog), converts X to PEP:
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a. Deduce the structure of intermediate X and provide a mechanism for its formation. You do not need to supply the full structures of the cofactor; just indicate the key portions of
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Chem+135+Spring+2010+-+Problem+Set+4+-+Answer+Key - CHEM...

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