Organic Chemistry
Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
Question
Book Icon
Chapter 25, Problem 3PP
Interpretation Introduction

Interpretation:

The possible mechanism for the formation of heterocyclic base on protected ribosylamine on the reaction with β-ethoxy-N-ethoxycarbonylacrylamide is to be represented.

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.

舧 Uridine ribonucleoside can be synthesized by the reaction of protected ribosylamine with β-ethoxy-N-ethoxycarbonylacrylamide. In this reaction, the compound β-ethoxy-N-ethoxycarbonylacrylamide is condensed to the amino group of 2,3,5-Tri-O-benzoyl-β-D-ribofuranosylamine >, which is subsequently converted into uridine.

Blurred answer
Students have asked these similar questions
Identify and provide a brief explanation of Gas Chromatography (GC) within the context of chemical analysis of food. Incorporate the specific application name, provide a concise overview of sample preparation methods, outline instrumental parameters and conditions ultilized, and summarise the outcomes and findings achieved through this analytical approach.
Identify and provide a concise explanation of the concept of signal-to-noise ratio (SNR) in the context of chemical analysis. Provide specific examples.
Identify and provide a concise explanation of a specific analytical instrument capable of detecting and quantifying trace compounds in food samples. Emphasise the instrumental capabilities relevant to trace compound analysis in the nominated food. Include the specific application name (eg: identification and quantification of mercury in salmon), outline a brief description of sample preparation procedures, and provide a summary of the obtained results from the analytical process.
Knowledge Booster
Background pattern image
Similar questions
SEE MORE QUESTIONS
Recommended textbooks for you
  • Text book image
    Organic Chemistry: A Guided Inquiry
    Chemistry
    ISBN:9780618974122
    Author:Andrei Straumanis
    Publisher:Cengage Learning
    Text book image
    Organic Chemistry
    Chemistry
    ISBN:9781305580350
    Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
    Publisher:Cengage Learning
    Text book image
    Organic Chemistry
    Chemistry
    ISBN:9781305080485
    Author:John E. McMurry
    Publisher:Cengage Learning
Text book image
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning
Text book image
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Text book image
Organic Chemistry
Chemistry
ISBN:9781305080485
Author:John E. McMurry
Publisher:Cengage Learning