CONVERTING FISCHER PROJECTIONS OF D MONOSACCHARIDES INTO HAWORTH STRUCTURES

Fisher projection

O H H HO H H OH H OH H HO H

O H OH
rotate C4-C5 clockwise

O H H HO H HOCH2 OH H OH H

*
rotate 90o clockwise

CH2OH H

OH H

OH CH2OH D-glucose
CH2 OH H H

H OH H OH CH2OH D-glucose

HO
H

O
OH H OH

OH D-glucose
CH2OH

O OH
H

H H

OH
H H

CH2OH H

OH H

HO H

OH OH

OH OH
H

HO O
H

*
OH H OH

O H

OH

alpha-D-glucose Haworth structure

In the Fischer projection: 1. Carbon-#1 is carbon-#1, the hemiacetal carbon (with a * ), in the Haworth structure 2. All of the atoms on the right are pointed down in the Haworth structure. 3. All of the atoms on the left are pointed up in the Haworth structure. 4. The CH2OH (the carbon-#6 in D-glucose) is pointed up in the Haworth structure 5. The OH attached to carbon-#5 (box around it) becomes part of the ring. 6. The linear Fischer projection becomes a cyclic hemiacetal in the Haworth structure.

In the Haworth Stucture: 1. Carbon-1 * is the anomeric carbon 2. The anomeric carbon is derived from the C=O in the Fischer projection. 3. Notice there are no carbonyls in the Haworth projection. 4. The carbonyl has become the hemiacetal group.

Drawing Haworth Projections of D-aldohexoses 1. Draw the Fischer projection and number the carbon atoms.

1CHO

H HO

2 3 4 5

OH H H OH

D-Galactose

HO H

6CH2OH

2. For an aldohexose draw the pyranose template for the Haworth projection and number the carbon atom. D-galactose is an aldohexose, so.. 3. Add hydroxyl groups to C2 C4 of the Haworth template. A. In the Fisher projection the hydroxyl groups on the right (only C2) are placed on a downward bond (a bond below the ring).
4

6 CH 5

2OH

O
1 2
6 CH 5
2

OH

O
1 2

4 3

OH

6 CH

B. In the Fisher projection, the hydroxyl groups on the left (only C3 and C4) are placed on an upward bond (a bond above the ring).

OH

HO 5
4

O
1 2

OH
3

OH

4. Add a hydroxyl group to C1 : downward for an alpha () hydroxyl (opposite side of ring as the CH2OH)

6 CH

OH

HO 5
4

O
1

OH
3

OH 2 OH
6 CH
2

upward for a beta () hydroxyl (same side of ring as the CH2OH)

HO 5
4

OH OH O
1 2

OH
3

OH

FINISHED!

Drawing Haworth Projections of D-aldopentoses 1. Draw the Fischer projection and number the carbon atoms.

1CHO

H HO

2 3 4

OH H OH

D-xylose

5CH2OH

2. For an aldopentose draw the furanose template for the Haworth projection and number the carbon atoms.

5 CH2OH

O
4 1 3 2

D-xylose is an aldopentose, so.. 3. Add hydroxyl groups to C2 C3 of the Haworth template. A. In the Fisher projection the hydroxyl groups on the right (only C2) are placed on a downward bond (a bond below the ring).

5 CH2OH

O
4 3 1 2

OH
5 CH2OH

B. In the Fisher projection, the hydroxyl groups on the left (only C3) are placed on an upward bond (a bond above the ring).

O
4

OH
3

1 2

OH
4. Add a hydroxyl group to C1 : downward for an alpha () hydroxyl (opposite side of ring as the CH2OH)
5 CH2OH

O
4 OH 3 2 1

OH

OH

5 CH2OH

OH
1 2

O
4 OH 3

upward for a beta () hydroxyl (same side of ring as the CH2OH)

OH

FINISHED!

Drawing Haworth Projections of D-ketohexoses 1. Draw the Fischer projection and number the carbon atoms. HO D-fructose H H

1CH2OH 2 3 4 5 6

O H OH OH CH2OH

2. For an ketohexose draw the furanose template for the Haworth projection and number the carbon atoms. Notice that carbon 1 is not present at this point and the OH at carbon 5 has become part of the ring.

6 CH2OH

O
5 4 3 2

D-fructose is a ketohexose, so.. 3. Add hydroxyl groups to C3 C4 of the Haworth template. A. In the Fisher projection the hydroxyl groups on the right (only C4) are placed on a downward bond (a bond below the ring).
6 CH2OH

O
5 4 3 2

OH
6 CH2OH

B. In the Fisher projection, the hydroxyl groups on the left (only C3) are placed on an upward bond (a bond above the ring).

O
5 4

OH
3

OH
4. Add a hydroxyl group to C2 : downward for an alpha () hydroxyl (opposite side of ring as the CH2OH)
6 CH2OH CH OH O 1 2 5 4 OH HO 2 3 OH
6 CH2OH OH O 5 4 OH HO 2 3 CH2OH 1

upward for a beta () hydroxyl (same side of ring as the CH2OH)

Notice that the carbon-1 CH2OH is placed opposite the OH at C2 FINISHED!