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Drawing Haworth Projections
Drawing Haworth Projections
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
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.
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
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.
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
OH
5 CH2OH 4 OH 3
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
CH OH O 1 2
upward for a beta () hydroxyl (same side of ring as the CHCH2OH 2OH) 4
OH