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    Chemistry 27: Practice Exam 3-A

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    Caroline
    1. The document is a practice exam for a chemistry course that contains instructions, an honor code statement, and 5 questions testing students' knowledge of organic reaction mechanisms and biochemical pathways. 2. The questions require students to draw curved arrow mechanisms for enzyme-catalyzed reactions involving cofactors like PLP and FAD, propose a mechanism for a small molecule bacterial signaling pathway, and complete an assembly line table and draw a mechanism for steps in the biosynthesis of the natural product romidepsin. 3. Students are instructed to show their work, provide only one answer per question, and sign the honor code before beginning the exam, which has a time limit of 83 minutes.

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    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd

    Chemistry 27: Practice Exam 3-A

    Uploaded by

    Caroline
    49 views10 pages
    1. The document is a practice exam for a chemistry course that contains instructions, an honor code statement, and 5 questions testing students' knowledge of organic reaction mechanisms and biochemical pathways. 2. The questions require students to draw curved arrow mechanisms for enzyme-catalyzed reactions involving cofactors like PLP and FAD, propose a mechanism for a small molecule bacterial signaling pathway, and complete an assembly line table and draw a mechanism for steps in the biosynthesis of the natural product romidepsin. 3. Students are instructed to show their work, provide only one answer per question, and sign the honor code before beginning the exam, which has a time limit of 83 minutes.

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    Chem Practice Exam

    Original Title

    Chem27_2017_PracticeExam-3A-Key-2

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    1. The document is a practice exam for a chemistry course that contains instructions, an honor code statement, and 5 questions testing students' knowledge of organic reaction mechanisms and biochemical pathways. 2. The questions require students to draw curved arrow mechanisms for enzyme-catalyzed reactions involving cofactors like PLP and FAD, propose a mechanism for a small molecule bacterial signaling pathway, and complete an assembly line table and draw a mechanism for steps in the biosynthesis of the natural product romidepsin. 3. Students are instructed to show their work, provide only one answer per question, and sign the honor code before beginning the exam, which has a time limit of 83 minutes.

    Copyright:

    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
    Download as pdf or txt
    49 views10 pages

    Chemistry 27: Practice Exam 3-A

    Uploaded by

    Caroline
    1. The document is a practice exam for a chemistry course that contains instructions, an honor code statement, and 5 questions testing students' knowledge of organic reaction mechanisms and biochemical pathways. 2. The questions require students to draw curved arrow mechanisms for enzyme-catalyzed reactions involving cofactors like PLP and FAD, propose a mechanism for a small molecule bacterial signaling pathway, and complete an assembly line table and draw a mechanism for steps in the biosynthesis of the natural product romidepsin. 3. Students are instructed to show their work, provide only one answer per question, and sign the honor code before beginning the exam, which has a time limit of 83 minutes.

    Copyright:

    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
    Download as pdf or txt
    of 10

    Practice Exam 3-A – ANSWER KEY

    Chemistry 27: Practice Exam 3-A


    Instructions: Please verify that your exam has 9 pages (including this one). Complete your
    answers for the following questions neatly, legibly, and concisely in the space provided below. If
    you provide multiple answers for the same question, place a box around the answer that you would
    like graded. Otherwise, your first answer (and nothing else) will be graded. For your convenience,
    scratch paper is attached at the back of the exam packet. You may remove the scratch paper, but
    work on these pages will NOT be graded! Be sure to manage your time wisely (83 minutes).

    Collaboration is not allowed on the exam. All answers submitted for evaluation must be exclusively
    the results of your own efforts. The use of molecular models is allowed but not necessary; no other
    exam aids, including calculators, will be allowed or required. On this exam, you may abbreviate
    iminium formation and hydrolysis, as well as transaldimination, by the conventions shown in
    lecture.

    This course endorses and promotes Harvard College’s expectations around academic integrity.
    Below is the text of the Honor Code for your review; all work for this course, including exams,
    should abide by these standards.

    The Harvard College Honor Code


    Members of the Harvard College community commit themselves to producing academic work of
    integrity – that is, work that adheres to the scholarly and intellectual standards of accurate
    attribution of sources, appropriate collection and use of data, and transparent acknowledgement of
    the contribution of others to their ideas, discoveries, interpretations, and conclusions. Cheating on
    exams or problem sets, plagiarizing or misrepresenting the ideas or language of someone else as
    one’s own, falsifying data, or any other instance of academic dishonesty violates the standards of
    our community, as well as the standards of the wider world of learning and affairs.

    I affirm my awareness of the standards of the Harvard College Honor Code.

    Signature:_______________________________________________________________

    Print Name: ____________________________________________________________

    HUID: __________________________________________________________________

    1 of 9
    Practice Exam 3-A – ANSWER KEY

    Chemistry 27: Practice Exam 3-A

    HUID: ____________________________________________

    Question Point Value Score


    1 10 _________
    2 17 _________
    3 23 _________
    4 22 _________
    5 28 _________

    Total 100

    Please circle your TF and section time below:

    Amanda Amanda Beverly Beverly Conor


    1:00 pm 8:30 am 8:30 am 7:00 pm 1:00 pm

    Conor Eileen Eileen Lydia


    2:30 pm 4:00 pm 7:00 pm 1:00 pm

    Lydia Nathaniel Nathaniel Mac


    2:30 pm 1:00 pm 4:00 pm 7:30 pm

    Matt Matt Mike Mike


    8:30 am 10:00 am 4:00 pm 11:30 am

    2 of 9
    Practice Exam 3-A – ANSWER KEY

    Question 1. (10 points) 3-oxodecabonyl-ACP and S-adenosyl methionine are used by bacteria to form
    the product below. The product serves as a small molecule communication signal between bacteria to
    coordinate population growth. Propose a curved-arrow mechanism for this reaction. Be sure to account
    for the identity and formation of all co-products.

    3 of 9
    Practice Exam 3-A – ANSWER KEY

    Question 2. (17 points) Draw the curved-arrow mechanism for the reaction shown below, which is
    performed by an FAD-dependent monooxygenase. You may use whatever co-substrate you see
    fit.

    4 of 9
    Practice Exam 3-A – ANSWER KEY

    Question 3. (23 points) The transformation shown below is catalyzed by a PLP-dependent


    enzyme. Provided a curved-arrow mechanism for this transformation.

    5 of 9
    Practice Exam 3-A – ANSWER KEY

    Question 4. (22 points total) Human oxidosqualene cyclase catalyzes the conversion of
    oxidosqualene to lanesterol. The Arabidopsis thaliana plant has thirteen different oxidosqualene
    cyclases. The products from two of these cyclases are shown below.

    4-a. (10 points) Starting from oxidosqualene, provide a mechanism for the formation of arabidiol. A
    suggestive conformation of oxidosqualene has been provided for you. While you do not have to
    show carbocation intermediates in the cyclization cascade, you must show all carbocation
    intermediates in any carbocation shift or termination steps.

    6 of 9
    Practice Exam 3-A – ANSWER KEY

    4-b. (12 points) The mechanisms for forming arabidiol and thalianol proceed through a common
    carbocation intermediate. Starting from the common intermediate, provide a curved-arrow
    mechanism for the formation of thalianol. Clearly indicate the stereochemistry and depict each
    carbocation intermediate as an individual step.

    7 of 9
    Practice Exam 3-A – ANSWER KEY

    Question 5. (28 points) Romidepsin, shown below, is biosynthesized by a PKS/NRPS hybrid


    assembly line. The romidepsin assembly line includes a unique tailoring domain, the
    aminotransferate (AmT) domain. A general example of the reaction catalyzed by the AmT domain
    is provided below.

    5-a. (15 points) Based on the structure of romidepsin, fill in the assembly line table below. The
    structures of some potentially useful starting materials have been provided for you. Note: There
    may be more spaces for modules in the table than are necessary.

    Starting
    Module AT KS KR DH ER ACP C A PCP E AmT TE
    Material
    0 Cys A PCP AmT
    1 MalCoA AT KS KR DH ACP
    2 MalCoA AT KS KR ACP
    3 Val C A PCP E
    4 Cys C A PCP E
    5 2,3-DHThr C A PCP
    6 Val C A PCP TE

    5-b. (4 points) Fill in the answers on the lines below:

    The function of the TE domain is: _______macrolactonization_________

    The number of molecules of ATP used in the assembly line is: ______5_______

    8 of 9
    Practice Exam 3-A – ANSWER KEY

    5-c. (9 points) Your assembly line table in part a should include at least one KS domain. Select
    the earliest KS domain in your table, and draw a mechanism for the step or steps catalyzed by the
    KS domain. Since the protein that catalyzes the formation of romidepsin is a hybrid PKS/NRPS
    assembly line enzyme, both the ACP and PCP domains have been provided below.

    9 of 9
    Practice Exam 3-A – ANSWER KEY

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