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Chapter 26: Q1P (page 1159)

In acidic solutions, nucleosides are hydrolyzed to a sugar and a heterocyclic base. Propose a mechanism for this reaction.

Short Answer

Expert verified

A compound containing a base bonded to d-ribose or to 2′-deoxy-d-ribose is called a nucleoside or these are glycosylamines made by attaching a nucleobase to a ribose or deoxyribose ring.

Adenosine

Guanosine

Deoxyadenosine

Deoxyguanosine

Step by step solution

01

Step 1:Nucleoside

A compound containing a base bonded to d-ribose or to 2′-deoxy-d-ribose is called a nucleoside or these are glycosylamines made by attaching a nucleobase to a ribose or deoxyribose ring.

Adenosine

Guanosine

Deoxyadenosine

Deoxyguanosine

02

Mechanism for the reaction

Nucleoside undergoes hydrolysis to form sugar and base. The example is represented as follows:

Hydrolysis of nucleoside

The mechanism for the reaction is as:

Mechanism

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Most popular questions from this chapter

a. Using the single-letter abbreviations for the amino acids in Table 21.2, write the sequence of amino acids in a tetrapeptide represented by the first four different letters in your first name. Do not use any letter twice. (Because not all letters are assigned to amino acids, you might have to use one or two letters in your last name.)

b. Write one of the sequences of bases in mRNA that would result in the synthesis of that tetrapeptide.

c. Write the sequence of bases in the sense strand of DNA that would result in the formation of that fragment of mRNA.

Human immunodeficiency virus (HIV) is the retrovirus that causes AIDS. AZT was one of the first drugs designed to interfere with retroviral DNA synthesis. When cells take up AZT, they convert it to AZT-triphosphate. Explain how AZT interferes with DNA synthesis.

Which of the following pairs of dinucleotides are present in equal amounts in DNA?

A. CC and GG

B. CG and GT

C. CA and TG

D. CG and AT

E. GT and CA

F. TA and AT

5-Bromouracil, a highly mutagenic compound (that is, a compound that causes changes in DNA), is used in cancer chemotherapy. When administered to a patient, it is converted to the triphosphate and incorporated into DNA in place of thymine, which it resembles sterically. Why does it cause mutations?

The amino acid sequences of peptide fragments obtained from a normal protein were compared with those obtained from the same protein synthesized by a defective gene. They were found to differ in only one peptide fragment. Their amino acid sequences are shown here:

Normal: Gln-Tyr-Gly-Thr-Arg-Tyr-Val

Mutant: Gln-Ser-Glu-Pro-Gly-Thr

a. What is the defect in DNA?

b. It was later determined that the normal peptide fragment is an octapeptide with a C-terminal Val-Leu. What is the C-terminal amino acid of the mutant peptide?
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