CONVERTING FISCHER PROJECTIONS OF D MONOSACCHARIDES INTO HAWORTH STRUCTURES Fisher projection O H OH H HO H

O H HO H H

H OH
rotate C4-C5 clockwise

O H HO H HOCH2

H OH H OH H *
rotate 90o clockwise

CH2OH H

OH

H OH OH CH2OH D-glucose

H OH H OH CH2OH D-glucose

HO
H

O
OH H OH

OH D-glucose
CH2OH

CH2 OH H H

O OH
H

H H

OH
H H

CH2OH H

OH

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.

CHO OH H H OH

H HO HO H

2 3 4 5 6

D-Galactose

CH2OH

2. For an aldohexose draw the pyranose 6 the Haworth projection and template for CH2OH number the5 carbon atom.

D-galactose is an aldohexose, so..

3 2

CH2OH 3. Add hydroxyl6groups to C2 C4 of the Haworth template. 5 O A. In the Fisher projection the hydroxyl 4 1 groups on the right (only C2) are placed on a downward bond (a bond below the 3 2 ring). OH

B. In the Fisher5projection, the hydroxyl HO groups on the leftO (only C3 and C4) are 1 placed on 4 upward bond (a bond an OH above the ring). 2 3
OH

6 CH

2OH

4. Add a6hydroxyl group to C1 : CH OH

2

downwardO an alpha () hydroxyl for (opposite side of ring as the CH2OH) 4 OH 1

3

HO 5

OH 2 OH

6 CH

2OH

upward for a betaO hydroxyl () 4 (same side ofOH as the CH2OH) ring 1
3 2

HO 5

OH

OH

FINISHED!

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

CHO OH H OH

H HO H

2 3 4 5

D-xylose

CH2OH

2. For an aldopentose draw the furanose template for the Haworth projection and 5 CH2OH number the carbon atoms.

2 D-xylose is3an aldopentose, so..

3. Add hydroxyl groups to C2 C3 of the 5 CH2OH Haworth template. A. In the Fisher O projection the hydroxyl groups 4 the right (only C2) are placed on 1 on a downward bond (a bond below the 2 ring). 3

OH
B. In the Fisher projection, the hydroxyl O groups on 4 OH (only1C3) are placed the left on an upward bond (a bond above the ring). 2 3
5 CH2OH

OH 4. Add a 5 CH OH group to C1 : hydroxyl

2

O downward for an alpha () hydroxyl OH 4 1 (opposite side of ring as the CH2OH)

3 2

OH

OH

5 CH2OH 4 OH 3

OH

1 upward for a beta () hydroxyl (same side of ring as the CH2OH) 2 OH

FINISHED!

Drawing Haworth Projections of D-ketohexoses 1. Draw the Fischer projection and number the carbon atoms. HO D-fructose H H 2. For an ketohexose draw the furanose template for the Haworth projection and 6 CH2OH number the carbon atoms. Notice that carbon 1 is notO present at this point and the OH at carbon 5 has become part of the 2 5 ring.
4 3

CH2OH O H OH OH CH2OH

2 3 4 5 6

D-fructose is a ketohexose, so.. 3. Add hydroxyl groups to C3 C4 of the 6 CH2OH Haworth template. A. In the Fisher O projection the hydroxyl 2 groups on the right (only C4) are placed 5 on a downward bond (a bond below the ring). 4 3

OH
B. In the Fisher projection, the hydroxyl O 2 groups on the left (only C3) are placed 5 OH on an upward bond (a bond above the ring). 4 3
6 CH2OH

OH 4. Add a hydroxyl group to C2 : CH OH

6
2

downward for an alpha () hydroxyl 5 (opposite side HOring as the CH2OH) of 2

4 OH 3 OH 6 CH2OH OH O 5 HO 2 3 1

CH OH O 1 2

upward for a beta () hydroxyl (same side of ring as the CHCH2OH 2OH) 4
OH

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