Organic Chemistry (8th Edition)
8th Edition
ISBN: 9780134042282
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Chapter 26.1, Problem 1P
In acidic solutions, nucleosides are hydrolyzed to a sugar and a heterocyclic base. Propose a mechanism for this reaction.
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In acidic solutions, nucleosides are hydrolyzed to a sugar and a heterocyclic base. Propose a mechanism for this reaction.
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Chapter 26 Solutions
Organic Chemistry (8th Edition)
Ch. 26.1 - In acidic solutions, nucleosides are hydrolyzed to...Ch. 26.1 - Draw the structure for each of the following: a....Ch. 26.3 - Indicate whether each functional group of the five...Ch. 26.3 - Prob. 4PCh. 26.3 - If one of the strands of DNA has the following...Ch. 26.4 - The 2',3-cyclic phosphodiester that is formed...Ch. 26.5 - Using a dark line for the original parental DNA...Ch. 26.7 - Why do both thymine and uracil specify the...Ch. 26.9 - If methionine is always the first amino acid...Ch. 26.9 - Four Cs occur in a row in the segment of mRNA...
Ch. 26.9 - UAA is a stop codon. Why does the UAA sequence in...Ch. 26.9 - Prob. 12PCh. 26.9 - Write the sequences of bases in the sense strand...Ch. 26.9 - List the possible codons on mRNA that speciy each...Ch. 26.10 - Adenine can be deaminated to hypoxanthine, and...Ch. 26.10 - Explain why thymine cannot be deaminated.Ch. 26.12 - Which of the following base sequences is most...Ch. 26 - What nonapeptide is coded for by the following...Ch. 26 - What is the sequence of bases in the template...Ch. 26 - Prob. 20PCh. 26 - A segment of DNA has 18 base pairs. It has 7...Ch. 26 - Name the following:Ch. 26 - Prob. 23PCh. 26 - Propose a mechanism for the following reaction:Ch. 26 - The first amino acid incorporated into a...Ch. 26 - Match the codon with the anticodon:Ch. 26 - a. Using the single-letter abbreviations for the...Ch. 26 - Which of the following pairs of dinucleotides are...Ch. 26 - Human immunodeficiency virus (HIV) is the...Ch. 26 - If a mRNA contained only U and G in random...Ch. 26 - Why is the codon a triplet rather than a doublet...Ch. 26 - RNAase, the enzyme that catalyzes the hydrolysis...Ch. 26 - The amino acid sequences of peptide fragments...Ch. 26 - Which cytosine in the following sense strand of...Ch. 26 - Prob. 36PCh. 26 - Sodium nitrite, a common food preservative (page...Ch. 26 - Why does DNA not unravel completely before...Ch. 26 - Staphylococcus nuclease is an enzyme that...
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- The enzyme that catalyzes the C-Cg bond cleavage reaction that converts serine to glycine removes the substituent (R) bonded to the a-carbon in the first step of the reaction. Starting with PLP bound to serine in an imine linkage, propose a mechanism for this reaction. (Hint: The first step involves removal of the proton from serine's OH group.)arrow_forwardGive a curved arrow mechanism for the hydrolysis of the dipeptide under an acidic condition. H20 H2N он H2N H2N. + H* OH dipeptide glycine alaninearrow_forwardAn octapeptide contains the following amino acids: Arg, Glu, His, Ile, Leu, Phe, Tyr, and Val. Carboxypeptidase treatment of the octapeptide forms Phe and a heptapeptide. Treatment of the octapeptide with chymotrypsin forms two tetrapeptides, A and B. Treatment of A with trypsin yields two dipeptides, C and D. Edman degradation cleaves the following amino acids from each peptide: Glu (octapeptide), Glu (A), Ile (B), Glu (C), and Val (D). Partial hydrolysis of tetrapeptide B forms Ile–Leu in addition to other products. Deduce the structure of the octapeptide and fragments A–D.arrow_forward
- Suggest a scheme you will follow to synthesize the dipeptide Ala-Glyarrow_forwardExposure to nitrous acid (see Section 19-16), sometimes found in cells, can convert cytosine to uracil.(a) Propose a mechanism for this conversion.(b) Explain how this conversion would be mutagenic upon replication.(c) DNA generally includes thymine, rather than uracil (found in RNA). Based on this fact, explain why the nitrous-acidinduced mutation of cytosine to uracil is more easily repaired in DNA than it is in RNA.*arrow_forwardThe hydrolysis of an ester can be sped up by both acidic and basic conditions. Aminolysis of an ester can be sped up by acidic conditions, but not by basic conditions. Explain why.arrow_forward
- 1. How would you synthesize adenosine monophosphate from ribose. Your synthetic path should be based on organic but NOT biosynthesis. OH NH2 HO HO HƠ OH HƠ OHarrow_forwardChorismate mutase is an enzyme that promotes a pericyclic reaction by forcing the substrate to assume the conformation needed for the reaction. The product of the pericyclic reaction is prephenate that is subsequently converted into the amino acids phenylalanine and tyrosine. What kind of a pericyclic reaction does chorismate mutase catalyze?arrow_forwardDraw a reaction mechanism to account for the formation of the dipeptide (cy = cyclohexyl)arrow_forward
- For the reactions below, predict the products and indicate the major product.arrow_forwardWhile there are proposals to explain the formation of sugars and nucleic acid bases separately, the following route demonstrated how they can be formed at the same time. H₂N N HO. H H₂N- N Q OH O OH H H₂N- EEN S H₂N R НО OH H3O+ b) Propose a mechanism for the formation of Q. c) Identify the most basic atom of Q and explain your answer. d) Propose a mechanism for the conversion of Q to R. e) Propose a mechanism for the reaction of R and S. OH OH OHarrow_forwardDescribe the hydrolysis reaction of aspartame after the treatment of acid (HCl) and base (NaOH).Write down the mechanism and identify the compounds.arrow_forward
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