Problem 2 To replicate, cells must increase their content of nucleic acids, which requires building blocks including pyrimidines. A key pyrimidine, UMP, is shown below HN. НО-Р-О. OH ОН ОН A. Using the arrow formalism, draw the reaction of UMP with ATP to produce UDP. For convenience, you can draw out only the reactive "triphosphate" portion of ATP (abbreviating adenosine as "Adeno"). B. With the help of an enzyme, uracil can react with phosphoribosylpyrophosphate (PRPP) (below) to form UMP. НО Но HOO HO O ОН Draw PRPP and circle the atom in PRPP where the reaction occurs. What is the hybridization of that atom? C. What is the reaction type? D. Using the PRPP that you drew in Part B, draw a sensible reaction mechanism using the arrow formalism, including the major carbon-containing intermediates (if any) and their relevant resonance forms (if any) (relevant meaning resonance forms related to the reaction mechanism, not in distant parts of the molecule). E. Propose a potential mechanism by which aspartate in the enzyme might facilitate the reaction. A quick drawing is recommended to illustrate your proposal. F. Imagine you try to carry out the above UMP-forming reaction in water without enzyme. Focusing exclusively on reactivity at the PRPP position that you circled in (B) (assuming the rest of the molecule does not react), what is the main product that you would expect? Why?

Biology: The Unity and Diversity of Life (MindTap Course List)
15th Edition
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Author:Cecie Starr, Ralph Taggart, Christine Evers, Lisa Starr
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Chapter8: Dna Structure And Function
Section: Chapter Questions
Problem 10SQ: Energy that drives the attachment of a nucleotide to the end of a growing strand of DNA comes from...
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Problem 2
To replicate, cells must increase their content of nucleic acids, which requires building blocks including
pyrimidines. A key pyrimidine, UMP, is shown below
`NH
НО-Р-О.
ОН
ОН ОН
A. Using the arrow formalism, draw the reaction of UMP with ATP to produce UDP. For
convenience, you can draw out only the reactive "triphosphate" portion of ATP (abbreviating
adenosine as "Adeno").
B. With the help of an enzyme, uracil can react with phosphoribosylpyrophosphate (PRPP) (below)
to form UMP.
НО НО
HOO
OH
Draw PRPP and circle the atom in PRPP where the reaction occurs. What is the hybridization of
that atom?
C. What is the reaction type?
D. Using the PRPP that you drew in Part B, draw a sensible reaction mechanism using the arrow
formalism, including the major carbon-containing intermediates (if any) and their relevant
resonance forms (if any) (relevant meaning resonance forms related to the reaction mechanism,
not in distant parts of the molecule).
E. Propose a potential mechanism by which aspartate in the enzyme might facilitate the reaction.
A quick drawing is recommended to illustrate your proposal.
F. Imagine you try to carry out the above UMP-forming reaction in water without enzyme.
Focusing exclusively on reactivity at the PRPP position that you circled in (B) (assuming the rest
of the molecule does not react), what is the main product that you would expect? Why?
Transcribed Image Text:Problem 2 To replicate, cells must increase their content of nucleic acids, which requires building blocks including pyrimidines. A key pyrimidine, UMP, is shown below `NH НО-Р-О. ОН ОН ОН A. Using the arrow formalism, draw the reaction of UMP with ATP to produce UDP. For convenience, you can draw out only the reactive "triphosphate" portion of ATP (abbreviating adenosine as "Adeno"). B. With the help of an enzyme, uracil can react with phosphoribosylpyrophosphate (PRPP) (below) to form UMP. НО НО HOO OH Draw PRPP and circle the atom in PRPP where the reaction occurs. What is the hybridization of that atom? C. What is the reaction type? D. Using the PRPP that you drew in Part B, draw a sensible reaction mechanism using the arrow formalism, including the major carbon-containing intermediates (if any) and their relevant resonance forms (if any) (relevant meaning resonance forms related to the reaction mechanism, not in distant parts of the molecule). E. Propose a potential mechanism by which aspartate in the enzyme might facilitate the reaction. A quick drawing is recommended to illustrate your proposal. F. Imagine you try to carry out the above UMP-forming reaction in water without enzyme. Focusing exclusively on reactivity at the PRPP position that you circled in (B) (assuming the rest of the molecule does not react), what is the main product that you would expect? Why?
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