Carbohydrate Structure Workbench

Draw sugars from memory, then convert, flip and link them.

Series
Drawing
Ring
Anomer

Your drawing

Template
Draw here with a mouse, stylus or finger.

Answer

Try this

  1. Draw the Fischer projection of D-glucose from memory, then reveal the answer. Which OH is on the left?
  2. Switch the drawing to Haworth and draw β-D-glucopyranose. Every group that was on the right in the Fischer projection should now point down.
  3. Switch the anomer to α. Only one group moves. Which one, and which way?
  4. Draw β-D-glucopyranose as a chair. How many groups are axial? Now try β-D-galactopyranose.
  5. Draw β-D-fructofuranose. Which carbon is anomeric, and which two groups does it carry?
  6. Pick sucrose. Why can you not choose α or β for it?
  7. Pick ribose and choose Envelope. Draw it with C-3 endo, then with C-2 endo. Which atom leaves the plane each time?

One sugar, three drawings

Click a carbon in any drawing to flip it. Point at a carbon to find it in the other two.

Series
Ring
Anomer

Fischer

Haworth

Chair

Build a glycosidic bond

The anomeric carbon of sugar 1 bonds to an OH of sugar 2.

Or build your own: choose any two sugars and the carbon that takes the bond.

1Sugar 1 gives its anomeric carbon

Series
Ring
Anomer

2Sugar 2 gives an OH

Series
Ring
Anomer
Bond to which carbon of sugar 2
Drawing

Product

Systematic name
Short form
Common name
Reducing sugar?

Try this

  1. Start from glucose and click C-4. What sugar did you make? Reset, then click C-2.
  2. Click C-5 of D-glucose. Why does the name change from D to L?
  3. Click C-1 in the Haworth drawing. What is this pair of sugars called, and what changes in the chair?
  4. Press L. How many stereocentres changed? What is the relationship to D-glucose?
  5. Flip the chair of β-D-glucopyranose and count the axial groups. Why is one chair so much more stable?
  6. Start from ribose and switch the pucker between C-3 endo and C-2 endo. Which one does RNA use, and which does B-form DNA use?
  7. Build lactose: galactose (β) as sugar 1, glucose as sugar 2, bond to carbon 4. Change sugar 1 to glucose. What is it now? Switch to α.
  8. Build sucrose: glucose (α) as sugar 1, fructose (β) as sugar 2, bond to carbon 2. Why is it not a reducing sugar?
  9. In the top picker choose lactose and click C-4 of sugar 1. Which disaccharide is it now? Then click C-1 of sugar 1.

Structures follow the usual textbook conventions. A side chain of two or more carbons outside a Haworth ring is drawn as a Fischer fragment. Equilibrium percentages are approximate values for water near room temperature.