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

H OH OH CH2OH D-glucose

H OH H OH CH2OH D-glucose

HO
H

O
OH H OH

H

OH D-glucose
CH2OH

CH2OH H H

O OH
H

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.

.

the hydroxyl HO groups on the leftO (only C3 and C4) are 1 placed on 4 OH an upward bond (a bond above the ring). Add a6 hydroxyl group to C1 : CH OH 2 downwardO an alpha (α) hydroxyl for (opposite side of ring as the CH2OH) 4 OH 1 3 HO 5 OH 2 OH 6 CH 2OH O upward for a beta (β) hydroxyl 4 OH (same side of ring as1the CH2OH) 3 2 HO 5 OH OH FINISHED! . 2 3 OH 6 CH 2OH 4. 1 CHO OH H H OH H HO HO H 2 3 4 5 6 D-Galactose CH2OH 2. so……. In the Fisher5 projection. 5 O A. 3 2 6 CH OH 3. O D-galactose is an aldohexose. Draw the Fischer projection and number the carbon atoms.. For an aldohexose draw the pyranose 6 the Haworth projection and template for CH2OH number the5carbon atom.Drawing Haworth Projections of D-aldohexoses 1. OH 4 1 B. 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). Add hydroxyl groups to C2 – C4 of the 2 Haworth template.

2 3 5 CH2OH OH 4. For an aldopentose draw the furanose template for the Haworth projection and 5 CH2OH number the carbon atoms. the hydroxyl O groups on4 OH (only C3) are placed the left 1 on an upward bond (a bond above the ring). A. Add a 5 CH OH group to C1 : hydroxyl 2 O downward for an alpha (α) hydroxyl OH 4 1 (opposite side of ring as the CH2OH) 3 2 OH OH 5 CH2OH 4 OH 3 O OH 1 upward for a beta (β) hydroxyl (same side of ring as the CH2OH) 2 OH FINISHED! . In the FisherO projection the hydroxyl groups 4 the right (only C2) are placed on 1 on a downward bond (a bond below the 2 ring). Add hydroxyl groups to C2 – C3 of the 5 CH2OH Haworth template. O 4 1 2 D-xylose is an aldopentose. 3 OH B. In the Fisher projection.. Draw the Fischer projection and number the carbon atoms. 1 CHO OH H OH H HO H 2 3 4 5 D-xylose CH2OH 2. so…….Drawing Haworth Projections of D-aldopentoses 1. 3 3.

For an ketohexose draw the furanose template for the Haworth projection and 6 CH2OH number the carbon atoms. 4 3 1 CH2OH O H OH OH CH2OH 2 3 4 5 6 D-fructose is a ketohexose.. HO D-fructose H H 2. Add a hydroxyl group to C2 : CH OH 6 2 downward for an alpha (α) hydroxyl 5 (opposite sideHO ring 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 (β) hydroxyl CH2OH (same side of ring 4 the CH2OH) as OH Notice that the carbon-1 CH2OH is placed opposite the OH at C2 FINISHED! . Notice that carbon 1 is not present at this point and O the OH at5carbon 5 has become part of the 2 ring. Draw the Fischer projection and number the carbon atoms. In the Fisher projection. Add hydroxyl groups to C3 – C4 of the 6 CH2OH Haworth template. 3. In the Fisher O projection the hydroxyl groups 5 the right 2 on (only C4) are placed on a downward bond (a bond below the ring). so……. the hydroxyl O 2 groups on the left OH C3) are placed (only 5 on an upward bond (a bond above the ring).Drawing Haworth Projections of D-ketohexoses 1. A. 4 3 6 CH2OH OH 4. 4 3 OH B.

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