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

b) Certain cyclic compounds are known to be conformationally similar to carbohydrates, although they are not themselves carbohydrates. One example is Compound C shown below, which could be imagined as adopting four possible conformations. In reality, however, only one of these is particularly stable. Circle the conformation you expect to be the most stable, and provide an explanation to justify your choice. For your explanation to be both convincing and correct, it must contain not only words, but also "cartoon" orbital drawings contrasting the four structures. Compound C Possible conformations (circle one): Дет

Lab Data The distance entered is out of the expected range. Check your calculations and conversion factors. Verify your distance. Will the gas cloud be closer to the cotton ball with HCI or NH3? Did you report your data to the correct number of significant figures? - X Experimental Set-up HCI-NH3 NH3-HCI Longer Tube Time elapsed (min) 5 (exact) 5 (exact) Distance between cotton balls (cm) 24.30 24.40 Distance to cloud (cm) 9.70 14.16 Distance traveled by HCI (cm) 9.70 9.80 Distance traveled by NH3 (cm) 14.60 14.50 Diffusion rate of HCI (cm/hr) 116 118 Diffusion rate of NH3 (cm/hr) 175.2 175.2 How to measure distance and calculate rate

For the titration of a divalent metal ion (M2+) with EDTA, the stoichiometry of the reaction is typically: 1:1 (one mole of EDTA per mole of metal ion) 2:1 (two moles of EDTA per mole of metal ion) 1:2 (one mole of EDTA per two moles of metal ion) None of the above