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Chem 128 – Introduction to Chemical Biology Mid-Term 2

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1(15 pts.) 1A. Fill in the blanks with the correct word or words below. From p. 143 in the textbook. With such a diverse portfolio of functions, random synthesis of different mRNAs would quickly prove disastrous for the cell. Instead, transcription by _RNA polymerase_______ is a tightly regulated event, dependent on the orchestration of __DNA sequences_________and__transcription factors________. Transcriptional regulation is driven by (1) ___growth OR cell division OR reproduction OR development_____ and (2) __metabolism or nutrient intake OR excretion of waste________. 1B. Answer the following question using a short, complete sentence. Under what circumstances can one borrow language from a journal article? The borrowed language must be offset from the main text using quotation marks or indentation, and the source must be cited. 2. (12 pts) Suggest a plausible arrow pushing reaction mechanism for the following reduction of disulfide bonds using a phosphine reagent. Hint: A phosphine (R3P) can act as a nucleophile. Cys R3P + SS HO R3P=O + 2Cys-SH Cys 2 H OH Cys Cys R3P: + SS S -:S Cys-SH Cys R3P+ H2O: Cys Cys Cys-SH H OH -:S Cys S :OH S R3P R3P=O R3P O+ O :OH2 Cys 2 HHH 3. (30 pts.) 3A. Draw the structure of the peptide QWFLT including correct stereochemistry. NH OHOHO H2NXNXXNXXNXXNX OH HO HO H 2N O OH 3B. On the structure you have drawn above in 3A, place an X over bonds subject to decreased rotational flexibility due to A1,3 strain. 3C. Explain why one bond marked X above is subject to decreased rotational flexibility using a resonance structure if necessary. O O- H2NN H2N+ HN HH H 2N O H 2N O These two small functionalities must be co-planar to minimize A1,3-strain 4. (23 pts) 4A. The following sequence encodes the first half of the protein streptavidin. Design PCR primers to amplifying the following DNA sequence. Your primers should have an annealing (melting) temperature as close to 55 °C as possible. Also, show the formula used to calculate the primer melting temperatures. TCAAGGAGCAATCGGATGAAAAATGTCTTGTCCCACATTGACGTGCTTCCAGGAGTACTG GGCGAAAGCATTCGAGTAATAGTAGAGCGCCGTGATCGTCGGCACGTTGTTCGTGATTTG Tm = 2 * (# of A/T’s) + 4 * (# of G/C’s) Forward primer: ATGTCAAGGAGCAATCGG (Tm = 18 + 36 = 54 °C) Reverse primer: CAAATCACGAACAACGTGC (Tm = 20 + 36 = 56 °C) 4B. Circle the start codon in the above sequence. 4C. Complete the following phrases by circling the correct words from the choices listed in bold. Streptavidin binds to (avidin / / nicotinamide / Vitamin B12) with very ( / weak) binding affinity. Streptavidin is an example of a(n) (α−helical /

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Chem 128 – Introduction to Chemical Biology

Midterm 2

Take a deep breath. Ok. Exhale and relax.
n Put your NAME and UCI ID number on the cover page, and complete the section below for your seat
number and signature.
n For maximum credit…
i) draw structures neatly
ii) show all elementary steps of reaction mechanisms
iii) clearly indicate where arrows begin and where arrows end.
n Now, turn the exam over and count to make sure that you have a complete examination. (There are 6
pages to the examination including the coversheet.)
n No electronic devices, textbooks, or notes can be used.
n Read through the exam before you begin. It will help you to budget your time.
n You may use the back of each page as scratch paper, but clearly label what you want to have graded.
• Your signature below indicates that you agree to abide by all U.C. Irvine regulations
concerning academic honesty. Your exam will not be graded unless this section is completed




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Seat




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Number:_______KEY_______________________




o.
rs e
Signature:______KEY_______________________
ou urc
___
o
aC s
vi y re
ed d
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PROBLEM POSSIBLE SCORE
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POINTS
1 15
2 12
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3 30
4 23
5 20
Bonus 5
Total 105 KEY

1
This study source was downloaded by 100000763811389 from CourseHero.com on 04-29-2021 03:56:22 GMT -05:00


https://www.coursehero.com/file/28966382/Midterm-2-2014-KEYpdf/

, Chem 128 – Introduction to Chemical Biology

1(15 pts.) 1A. Fill in the blanks with the correct word or words below. From p. 143 in the textbook.

With such a diverse portfolio of functions, random synthesis of different mRNAs would quickly

prove disastrous for the cell. Instead, transcription by _RNA polymerase_______ is a tightly regulated

event, dependent on the orchestration of __DNA sequences_________and__transcription factors________.

Transcriptional regulation is driven by (1) ___growth OR cell division OR reproduction OR

development_____ and (2) __metabolism or nutrient intake OR excretion of waste________.

1B. Answer the following question using a short, complete sentence.
Under what circumstances can one borrow language from a journal article?

The borrowed language must be offset from the main text using quotation marks or indentation, and the
source must be cited.




m
er as
co
eH w
2. (12 pts) Suggest a plausible arrow pushing reaction mechanism for the following reduction of disulfide




o.
rs e
bonds using a phosphine reagent. Hint: A phosphine (R3P) can act as a nucleophile.
Cys
ou urc
R3P + S S R3P=O + 2 Cys-SH
Cys H2O
o
aC s
vi y re


OH
H
Cys Cys
R 3P: + S S S -:
S Cys-SH
Cys R 3P + Cys
ed d




Cys-SH
ar stu




H 2O :
is




Cys Cys OH
S H
S R 3P=O
Th




:OH 2 R 3P -:
R 3P S
O+ O :OH 2 Cys
H H H
sh




2
This study source was downloaded by 100000763811389 from CourseHero.com on 04-29-2021 03:56:22 GMT -05:00


https://www.coursehero.com/file/28966382/Midterm-2-2014-KEYpdf/
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