Fructose is found in many fruits. From memory, draw fructose in

  1. the Fischer projection of the open chain.
  2. The most stable chair conformation of the most stable pyranose anomer.
  3. The Haworth projection of the most stable pyranose anomer

Short Answer

Expert verified

Fructose is a ketohexose which contain a ketone group. It is used as a sweetening agent in many confectionaries and also as a substitute of cane sugar.

Step by step solution

01

Fructose

Fructose is a ketohexose which contain a ketone group. It is used as a sweetening agent in many confectionaries and also as a substitute of cane sugar.

02

Pyranose

Pyranose is a six-membered cyclic hemiacetal whose name is derived from the six-membered cyclic ether pyran.

03

Anomers

The diastereomers resulting from cyclisation are known as anomers. They differ only in the configuration around first carbon (C1) which is referred to as the anomeric carbon (hemiacetal carbon atom).

04

Identifying α  and β  anomers of pyranoses

For α-anomer, hydroxy group (-OH) on the anomeric carbon is down (axial position) while for β - anomer, hydroxy group (-OH) on the anomeric carbon is up (equatorial position). Again, for anomer, the anomeric hydroxy (-OH) group is placed trans to the terminal -CH2OH group while for β- anomer, the anomeric hydroxy (-OH) group is placed cis to the terminal -CH2OH group.

05

 Step 5: Structure of various forms of fructose

a) Sugars in their open chain form is given by the Fischer projection where the vertical solid lines show the connection of different carbon atoms present in a sugar while the horizontal solid lines show carbon-oxygen and carbon- hydrogen bonds.


b) The most stable chair conformation of the most stable pyranose anomer of fructose is β-D- fructopyranose . In chair conformation of β-D- fructopyranose , the anomeric carbon is C1 . The hydroxy group ( -OH ) on the anomeric carbon is up (equatorial position).

c) The Haworth projection of β-D- fructopyranose is represented by the figure below:


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Most popular questions from this chapter

After a series of Kiliani–Fischer syntheses on (+)-glyceraldehyde, an unknown sugar is isolated from the reaction mixture. The following experimental information is obtained:

(1) Molecular formula C6H12O6

(2) Undergoes mutarotation.

(3) Reacts with bromine water to give an aldonic acid.

(4) Reacts with HNO3 to give an optically active aldaric acid.

(5) Ruff degradation followed by HNO3 oxidation gives an optically inactive aldaric acid. (6) Two Ruff degradations followed by HNO3 oxidation give meso-tartaric acid.

(7) When the original sugar is treated with CH3I and Ag2O, a pentamethyl derivative is formed. Hydrolysis gives a tetramethyl derivative with a free hydroxy group on C5.

(a) Draw a Fischer projection for the open-chain form of this unknown sugar. Use Figure 23-3 to name the sugar.

(b) Draw the most stable conform

Draw the structures (using chair conformations of pyranoses) of the following disaccharides.

(a) 4-O-(α -D-glucopyranosyl)-D-galactopyranose

(b) α -D-fructofuranosyl-β -D-mannopyranoside

(c) 6-O-(β -D-galactopyranosyl)-D-glucopyranose

Does lactose mutarotate? Is it a reducing sugar? Explain. Draw the two anomeric forms of lactose.

Draw and name the enantiomers of the sugars shown in Figure 23-2. Give the relative configuration (D or L) and the sign of the rotation in each case.

Raffinose is a trisaccharide (C18H32O16) isolated from cottonseed meal. Raffinose does not reduce Tollens reagent, and it does not mutarotate. Complete hydrolysis of raffinose gives D-glucose, D-fructose, and D-galactose. When raffinose is treated with invertase, the products are D-fructose and a reducing disaccharide called melibiose. Raffinose is unaffected by treatment with a-galactosidase, but an α -galactosidase hydrolyzes it to D-galactose and sucrose. When raffinose is treated with dimethyl sulfate and base followed by hydrolysis, the products are 2,3,4-tri-O-methylglucose, 1,3,4,6-tetra-O-methylfructose, and 2,3,4,6-tetra-O-methylgalactose. Determine the complete structures of raffinose and melibiose and give a systematic name for melibiose.

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