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  • Biochem 131 Problem Set

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    Janrick See
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    The document contains 4 questions from a biochemistry problem set on the biosynthesis of amino acids: 1. Phosphohomoserine requires PLP rather than direct elimination of phosphate because PLP acts as an electrophilic catalyst in the reaction. 2. The mechanism for the PLP-dependent reaction of O-succinylhomoserine with cysteine involves PLP forming a Schiff base intermediate with cysteine, displacing succinate and forming cystathionine. 3. A simple acid-catalyzed nucleophilic attack by cysteine on succinylhomoserine is unfavorable because the conjugate base of cysteine is a weak nucleophile at physiological pH.

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    The document contains 4 questions from a biochemistry problem set on the biosynthesis of amino acids: 1. Phosphohomoserine requires PLP rather than direct elimination of phosphate because PLP acts as an electrophilic catalyst in the reaction. 2. The mechanism for the PLP-dependent reaction of O-succinylhomoserine with cysteine involves PLP forming a Schiff base intermediate with cysteine, displacing succinate and forming cystathionine. 3. A simple acid-catalyzed nucleophilic attack by cysteine on succinylhomoserine is unfavorable because the conjugate base of cysteine is a weak nucleophile at physiological pH.

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    14 views1 page

    Biochem 131 Problem Set

    Uploaded by

    Janrick See
    The document contains 4 questions from a biochemistry problem set on the biosynthesis of amino acids: 1. Phosphohomoserine requires PLP rather than direct elimination of phosphate because PLP acts as an electrophilic catalyst in the reaction. 2. The mechanism for the PLP-dependent reaction of O-succinylhomoserine with cysteine involves PLP forming a Schiff base intermediate with cysteine, displacing succinate and forming cystathionine. 3. A simple acid-catalyzed nucleophilic attack by cysteine on succinylhomoserine is unfavorable because the conjugate base of cysteine is a weak nucleophile at physiological pH.

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    BIOCHEM 131

    PROBLEM SET : BIOSYNTHESIS OF AMINO ACIDS

    1. Why does the elimination of phosphate from phosphohomoserine require PLP rather than occurring directly? Answer in 3 sentences or less. 2. Show the mechanism for the PLP-dependent reaction of O-succinylhomoserine with cysteine to give cystathionine. 3. Follow-up question from # 2: Why is a simple acid-catalyzed nucleophilic attack by cysteine an unfavorable reaction mechanism (see figure below)? Answer in 3 sentences or less.
    H 3C H N

    O H A H N

    CH2 OPO3 2-

    Succ-O SH H

    CO 2-

    NH 3+ CO 2-

    4. Methionine synthetase is a cobalamin-dependent enzyme that catalyzes the methyl transfer from 5-methyltetrahydrofolate to homocysteine via formation of methyl-cobalamin protein complex. If the methyl group is electrophilic, how can it bind to cobalt ion of cobalamin? Answer in 3 sentences or less.

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