Biochemistry: Concepts and Connections (2nd Edition)
Biochemistry: Concepts and Connections (2nd Edition)
2nd Edition
ISBN: 9780134641621
Author: Dean R. Appling, Spencer J. Anthony-Cahill, Christopher K. Mathews
Publisher: PEARSON
Question
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Chapter 9, Problem 1P

(a)

Interpretation Introduction

Interpretation:

The Haworth projections for

  Biochemistry: Concepts and Connections (2nd Edition), Chapter 9, Problem 1P , additional homework tip  1

in a-furanose form should be identified along with the name of the sugar.

Concept introduction:

A Haworth projection is common way to represent the cyclic structure of monosaccharides.

Five and six membered hemiacetals are represented as planar pentagons or hexagons.

  α -form of the Haworth projection indicates, the exocyclic O group at the anomeric centre is on the opposite face as to the CH2OH group.

  β -form of the Haworth projection, the exocyclic O group at the anomeric centre is on the same face as to the CH2OH group.

In the Haworth projection - CH2OH group is present in the RIGHT side of the ring is called D- form.

In the Haworth projection - CH2OH group is present in the LEFT side of the ring is called L- form.

For example:

Haworth projections of glucose:

  Biochemistry: Concepts and Connections (2nd Edition), Chapter 9, Problem 1P , additional homework tip  2

Pictorial representation:

  α-D-Xylofuranose

  Biochemistry: Concepts and Connections (2nd Edition), Chapter 9, Problem 1P , additional homework tip  3

(a)

Expert Solution
Check Mark

Explanation of Solution

The given structure is as follows.

  Biochemistry: Concepts and Connections (2nd Edition), Chapter 9, Problem 1P , additional homework tip  4

Above structure has 5 carbons and on 3rd carbon –OH group is present in the left side of the carbon chain. Therefore, the name of the sugar is α-D-Xylofuranose .

Let’s draw the Haworth projection of α-D-Xylofuranose .

In the D form of Haworth projection, the exocyclic O group at the anomeric centre is on the opposite face as to the CH2OH group.

  Biochemistry: Concepts and Connections (2nd Edition), Chapter 9, Problem 1P , additional homework tip  5

(b)

Interpretation Introduction

Interpretation:

The Haworth projections for L isomer of (a) should be drawn.

Concept introduction:

A Haworth projection is common way to represent the cyclic structure of monosaccharides.

Five and six membered hemiacetals are represented as planar pentagons or hexagons.

  α form of the Haworth projection indicates, the exocyclic O group at the anomeric centre is on the opposite face as to the CH2OH group.

  β form of the Haworth projection, the exocyclic O group at the anomeric centre is on the same face as to the CH2OH group.

In the Haworth projection - CH2OH group is present in the RIGHT side of the ring is called D- form.

In the Haworth projection - CH2OH group is present in the LEFT side of the ring is called L- form.

For example:

Haworth projections of glucose:

  Biochemistry: Concepts and Connections (2nd Edition), Chapter 9, Problem 1P , additional homework tip  6

Pictorial representation:

  β - L - Xylofuranose

  Biochemistry: Concepts and Connections (2nd Edition), Chapter 9, Problem 1P , additional homework tip  7

(b)

Expert Solution
Check Mark

Explanation of Solution

In L form of Haworth projection, the exocyclic O group at the anomeric centre is on the same face as to the CH2OH group.

  Biochemistry: Concepts and Connections (2nd Edition), Chapter 9, Problem 1P , additional homework tip  8

(c)

Interpretation Introduction

Interpretation:

The Haworth projections for a-D-Glc-NAc should be drawn.

Concept introduction:

A Haworth projection is common way to represent the cyclic structure of monosaccharides.

Five and six membered hemiacetals are represented as planar pentagons or hexagons.

  α form of the Haworth projection indicates, the exocyclic O group at the anomeric centre is on the opposite face as to the CH2OH group.

  β form of the Haworth projection, the exocyclic O group at the anomeric centre is on the same face as to the CH2OH group.

In the Haworth projection - CH2OH group is present in the RIGHT side of the ring is called D- form.

In the Haworth projection - CH2OH group is present in the LEFT side of the ring is called L- form.

For example:

Haworth projections of glucose:

  Biochemistry: Concepts and Connections (2nd Edition), Chapter 9, Problem 1P , additional homework tip  9

Pictorial representation:

  α-D-GlcNAC

  (N-acetyl-α -D-Glucoseaminide)

  Biochemistry: Concepts and Connections (2nd Edition), Chapter 9, Problem 1P , additional homework tip  10

(c)

Expert Solution
Check Mark

Explanation of Solution

  α-D-GlcNAC

  (N-acetyl-α -D-Glucoseaminide)

In this compound,  α-D-Glucose has acetanilide group at the 3rd carbon. The structure is as follows.

  Biochemistry: Concepts and Connections (2nd Edition), Chapter 9, Problem 1P , additional homework tip  11

(d)

Interpretation Introduction

Interpretation:

The Haworth projections for a-D-Fructofuranose should be drawn.

Concept introduction:

A Haworth projection is common way to represent the cyclic structure of monosaccharides.

Five and six membered hemiacetals are represented as planar pentagons or hexagons.

  α form of the Haworth projection indicates, the exocyclic O group at the anomeric centre is on the opposite face as to the CH2OH group.

  β form of the Haworth projection, the exocyclic O group at the anomeric centre is on the same face as to the CH2OH group.

In the Haworth projection - CH2OH group is present in the RIGHT side of the ring is called D- form.

In the Haworth projection - CH2OH group is present in the LEFT side of the ring is called L- form.

For example:

Haworth projections of glucose:

  Biochemistry: Concepts and Connections (2nd Edition), Chapter 9, Problem 1P , additional homework tip  12

Pictorial representation:

  α - D - Fructofuranose

  Biochemistry: Concepts and Connections (2nd Edition), Chapter 9, Problem 1P , additional homework tip  13

(d)

Expert Solution
Check Mark

Explanation of Solution

  α - D - Fructofuranose

It has 5 member furanose ring. The structure is as follows.

  Biochemistry: Concepts and Connections (2nd Edition), Chapter 9, Problem 1P , additional homework tip  14

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