(a) An aliphatic aminoglycoside is relatively stable to base, but it is quickly hydrolyzed bydilute acid. Propose a mechanism for the acid-catalyzed hydrolysis.NHHCH2RR2NH2 + sugarRHHOH OHOH Oan aliphatic ribosideH3O+ +(b) Ribonucleosides are not so easily hydrolyzed, requiring relatively strong acid.Using your mechanism for part (a), show why cytidine and adenosine (for example)are not so readily hydrolyzed. Explain why this stability is important for livingorganisms.

Chemistry: Principles and Reactions
8th Edition
ISBN:9781305079373
Author:William L. Masterton, Cecile N. Hurley
Publisher:William L. Masterton, Cecile N. Hurley
Chapter23: Organic Polymers, Natural And Synthetic
Section: Chapter Questions
Problem 31QAP: On complete hydrolysis, a polypeptide gives two alanine, one leucine, one methionine, one...
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(a) An aliphatic aminoglycoside is relatively stable to base, but it is quickly hydrolyzed by
dilute acid. Propose a mechanism for the acid-catalyzed hydrolysis.
N
H
H
CH2
R
R2NH2 + sugar
R
H
H
OH OH
OH O
an aliphatic riboside
H3O+ +
(b) Ribonucleosides are not so easily hydrolyzed, requiring relatively strong acid.
Using your mechanism for part (a), show why cytidine and adenosine (for example)
are not so readily hydrolyzed. Explain why this stability is important for living
organisms.

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