Organic Chemistry
7th Edition
ISBN: 9780321803221
Author: Paula Y. Bruice
Publisher: Prentice Hall
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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.
Researchers analysed a glycopeptide (a peptide carrying one or several oligosaccharide
groups) and determined both the sequence of the peptide and the sequence of the sugar molecule. The
latter was identified as a diholoside coupled to the peptide by an osidic bond. The systematic name
of this sugar is:
B-D-glucopyranosyl-(1→4)-ß-D-galactopyranose.
: Represent the chemical formula of this diholoside in a way that all oses are
Question 1
represented according to the Haworth convention. Apart from the furane and/or pyrane cycles all
atoms of this molecule must be given.
The enzyme that catalyzes the Ca ¬ Cb bond cleavage reaction that converts serine to glycine removes thesubstituent (R) bonded to the a-carbon in the first step of the reaction. Starting with PLP bound to serine inan imine linkage, propose a mechanism for this reaction. (Hint: The first step involves removal of the protonfrom serine’s OH group.)
Chapter 26 Solutions
Organic Chemistry
Ch. 26.1 - In acidic solutions, nucleosides are hydrolyzed to...Ch. 26.1 - Draw the structure for each of the following: a....Ch. 26.2 - Prob. 3PCh. 26.3 - Indicate whether each functional group of the five...Ch. 26.3 - Prob. 5PCh. 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. 13PCh. 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 - Name the following:Ch. 26 - What nonapeptide is coded for by the following...Ch. 26 - What is the sequence of bases in the template...Ch. 26 - Prob. 22PCh. 26 - Prob. 23PCh. 26 - Prob. 24PCh. 26 - Propose a mechanism for the following reaction:Ch. 26 - A segment of DNA has 18 base pairs. It has 7...Ch. 26 - Match the codon with the anticodon:Ch. 26 - Prob. 28PCh. 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...Ch. 26 - The first amino acid incorporated into a...
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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_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_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_forward
- Suggest a scheme you will follow to synthesize the dipeptide Ala-Glyarrow_forwardDuring base excision repair, DNA glycosylase cleaves theN-glycosidic link between the altered base and the deoxyribose component of the nucleotide. Draw a typical nucleotideand indicate which bond is cleaved.arrow_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_forward
- Treatment of adenosine with nitrous acid gives a nucleoside known as inosine. Suggest a reasonable mechanism for this reaction.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_forwardGive the major product that is formed when the primary hydroxyl group of the followingmonosaccharide reacts with propionic anhydride.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_forwardContrast the structure of glycogen and chitin. Drag the appropriate items to their respective rows. Glycogen Chitin Monomers connect by B-1,4-glycosidic linkages Monomers connect by alpha-1,4-glycosidic linkages Polymers interact with one another via hydrogen bonds Consists of modified glucose residues (NAG) Contains branches arising from alpha-1,6-glycosidic linkages Consists of glucose residuesarrow_forwardDraw a diagram of the linear and ring structures of ribose. Show the biochemical mechanism of cyclization of each and name the resultant ring – including the ring type & anomeric carbon designation. Draw and name an amine version, reduced version, and oxidized version, either in ring or Fisher projection.arrow_forward
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