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Organic And Biological Chemistry

7th Edition
STOKER + 1 other
ISBN: 9781305081079

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Chapter
Section
BuyFindarrow_forward

Organic And Biological Chemistry

7th Edition
STOKER + 1 other
ISBN: 9781305081079
Textbook Problem

In which of the following disaccharides is the bonding between monosaccharides units “head-to-head” rather than “head-to-tail”?

  1. a. lactose
  2. b. cellobiose
  3. c. maltose
  4. d. no correct response

Interpretation Introduction

Interpretation: The disaccharide in which the bonding between monosaccharide occurs “head-to-head” rather than “head-to-tail” has to be predicted.

Concept introduction: The bond formed between the OH group of hemiacetal carbon of one monosaccharide and an OH group on the other monosaccharide is called a glycosidic linkage.  The glycosidic linkage in maltose, cellobiose and lactose is different from that in sucrose.

Explanation

Reason for correct option:

The glycosidic linkage in maltose, cellobiose and lactose is characterized as “head-to-tail” linkage.  In these three disaccharides, the carbon 1 of a monosaccharide is bonded with the carbon 4 of the other monosaccharide.  It is known as “head-to-tail” linkage.  The “head-to-tail” linkage in maltose, cellobiose and lactose is shown below.

But the bonding between the monosaccharide units in sucrose is different.  The structural units of monosaccharides present in sucrose are α-D-glucose and β-D-fructose.  These monosaccharides are joined together by an α,β(12) glycosidic linkage

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