The reason for the susceptibility of nucleosides to acidic hydrolysis and the mechanism of this hydrolysis is to be explained. Concept introduction: 舧 Electrophiles are electron-deficient species, which has positive or partially positive charge. Lewis acids are electrophiles, which accept electron pair. 舧 Nucleophiles are electron-rich species, which has negative or partially negative charge. Lewis bases are nucleophiles, which donate electron pair. 舧 A nucleoside consists of a nucleobase (also termed as nitrogenous base) and a five-carbon sugar (either ribose or deoxyribose). 舧 A nucleotide consists of a nucleobase (also termed as nitrogenous base), a five-carbon sugar (either ribose or deoxyribose) and one or more phosphate groups. 舧 In a nucleoside, the anomeric carbon is linked through a glycosidic bond to the N9 of a purine or N1 of a pyrimidine. 舧 Examples of nucleosides include cytidine, uridine, adenosine, guanosine and thymidine. 舧 Sugar (ribose/deoxyribose) and nitrogenous bases are linked through N-glycosidic bonds. 舧 These glycosidic bonds are formed by condensation reaction of first carbon of sugar molecule with the nitrogen atom ( N1 of pyrimidines and N9 of purines) of the nitrogenous base. 舧 This particular glycosidic bond is stable in basic solutions, but readily hydrolyzes in the presence of acids.

Question

Want to see the full answer?

Answer 1

Question

Chapter 25, Problem 2PP

Interpretation Introduction

Interpretation:

The reason for the susceptibility of nucleosides to acidic hydrolysis and the mechanism of this hydrolysis is to be explained.

Concept introduction:

舧 Electrophiles are electron-deficient species, which has positive or partially positive charge. Lewis acids are electrophiles, which accept electron pair.

舧 Nucleophiles are electron-rich species, which has negative or partially negative charge. Lewis bases are nucleophiles, which donate electron pair.

舧 A nucleoside consists of a nucleobase (also termed as nitrogenous base) and a five-carbon sugar (either ribose or deoxyribose).

舧 A nucleotide consists of a nucleobase (also termed as nitrogenous base), a five-carbon sugar (either ribose or deoxyribose) and one or more phosphate groups.

舧 In a nucleoside, the anomeric carbon is linked through a glycosidic bond to the N9 of a purine or N1 of a pyrimidine.

舧 Examples of nucleosides include cytidine, uridine, adenosine, guanosine and thymidine.

舧 Sugar (ribose/deoxyribose) and nitrogenous bases are linked through N-glycosidic bonds.

舧 These glycosidic bonds are formed by condensation reaction of first carbon of sugar molecule with the nitrogen atom (N1 of pyrimidines and N9 of purines) of the nitrogenous base.

舧 This particular glycosidic bond is stable in basic solutions, but readily hydrolyzes in the presence of acids.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Students have asked these similar questions

Don't used Ai solution

What is the absorption spectrum of a solution of naphthalene in benzene , and the vibronic transitions responsible for the vibrational fine structure ?

3. Titanium(III) chloride can be used to catalyze the polymerization of ethylene. It is prepared by hydrogen reduction of Titanium(IV) chloride. Reaction of hydrogen gas with titanium(IV) chloride gas produces solid titanium(III) chloride and hydrogen chloride gas. (a) Write a BALANCED chemical reaction for the preparation of titanium(III) chloride (b) A 250 L reaction vessel at 325°C is filled with hydrogen gas to a pressure of 1.3 atm. Titanium(IV) chloride is then added to bring the total pressure to 3.00 atm. How many grams of titanium(III) chloride will be produced after completion of the reaction? (c) What will be the pressure of the resulting hydrogen chloride gas that is also produced?