EBK ORGANIC CHEMISTRY
EBK ORGANIC CHEMISTRY
8th Edition
ISBN: 8220102744127
Author: Bruice
Publisher: PEARSON
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Chapter 20, Problem 68P
Interpretation Introduction

Interpretation:

A structure for the disaccharide is to be proposed.

Concept Introduction:

The disaccharides formed from the monosaccharide units that are connected with each other through the glycosidic bonds.  Glycosidic bonds are the type of covalent bonds.  The condensation reactions are also involved in the formation of disaccharides.  The elimination of water molecules takes place during the condensation reactions.

Monosaccharide units are made from the biomolecules that comprise carbon, oxygen and hydrogen atoms.  These molecules cannot be broken into the simpler compounds.  The numbers of isomers are obtained from biomolecules due to the chiral nature of carbon atoms.

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An unknown disaccharide gives a positive Tollens’ test. A glycosidase hydrolyzes it to D-galactose and D-mannose. When the disaccharide is treated with methyl iodide and Ag2O and then hydrolyzed with dilute HCl, the products are 2,3,4,6-tetra-O-methylgalactose and 2,3,4-tri-O-methylmannose. Propose a structure for the disaccharide.
Human milk contains the oligosaccharide 2′-fucosyllactose (α-Lfucose-(1→2)-β-D-galactose-(1→4)-Dglucose), which may help protect the newborn from bacterial infections. Draw the structure of this oligosaccharide.
If the following oligosaccharide was treated with an enzyme that cleaved only a 1,4 glycosidic bonds, what would be the products? OH CH₂OH OH CH₂OH OH CH₂OH OH OH OH OH CH₂OH CH₂OH a monosaccharide and a pentasaccharide a disaccharide and a tetrasaccharide two trisaccharides a monosaccharide, a disaccharide, and a trisaccharide O three disaccharides OH CH₂OH OH CH₂OH OH OH OH OH

Chapter 20 Solutions

EBK ORGANIC CHEMISTRY

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