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Chapter 23: Q39P (page 1237)

Is gentiobiose a reducing sugar? Does it mutarotate? Explain your reasoning.

Short Answer

Expert verified

Gentiobiose can mutarotate because it has free anomeric end which is shown by the figure below.

Step by step solution

01

A concept:

Gentiobiose is a disaccharide in which two glucose units are linked together by a 尾-1,6 glycosidic linkage. The anomeric carbon of one sugar is linked to the oxygen of the terminal carbon (C6) of another sugar in 1,6 linkage.

02

Explain is gentiobiose a reducing sugar or not:

Gentiobiose is a reducing sugar since it has only one of its two anomeric carbon atoms involved in the glycosidic bond. This means that gentiobiose can be converted to an open chain form with an aldehyde (-CHO) group.

Gentiobiose can mutarotate because it has free anomeric end which is shown by the figure below.

Free anomeric end which is able to mutarotate.

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Most popular questions from this chapter

Question: Exposure to nitrous acid (see Section 19-16), sometimes found in cells, can convert cytosine to uracil.

  1. Propose a mechanism for this conversion.
  2. Explain how this conversion would be mutagenic upon replication.
  3. DNA generally includes thymine, rather than uracil(found in RNA). Based on this fact, explain why the nitrous acid-induced mutation of cytosine to uracil is more easily repaired in DNA than it is in RNA.

The Wohl degradation, an alternative to the Ruff degradation, is nearly the reverse of the Kiliani-Fischer synthesis. The aldose carbonyl group is converted to the oxime, which is dehydrated by acetic anhydride to the nitrile (a cyanohydrin). Cyanohydrin formation is reversible, and a basic hydrolysis allows the cyanohydrin to lose HCN. Using the following sequence of reagents, give equations for the individual reaction in the Wohl degradation of D-arabinose to D-erythrose. Mechanisms are not required.

(1) hydroxylamine hydrochloride

(2) acetic anhydride

(3) OH-,H2O

a) Draw D-allose, the C3 epimer of glucose.

b) Draw D-talose, the C2 epimer of D-galactose.

c) Draw D-idose, the C3 epimer of D-talose. Now compare your answers with Figure 23-3.

d) Draw the C4 鈥渆pimer鈥� of D-xylose. Notice that this 鈥渆pimer鈥� is actually an L-series sugar, and we have seen its enantiomer. Give the correct name for this L-series sugar.

When the gum of the shrub Sterculia setigera is subjected to acidic hydrolysis, one of the water-soluble components of the hydrolysate is found to be tagatose. The following information is known about tagatose:

(1) Molecular formula C6H12O6

(2) Undergoes mutarotation.

(3) Does not react with bromine water.

(4) Reduces Tollens reagent to give d-galactonic acid and d-talonic acid.

(5) Methylation of tagatose (using excess CH3 I and Ag2O) followed by acidic hydrolysis gives 1,3,4,5-tetra-O-methyltagatose.

(a) Draw a Fischer projection structure for the open-chain form of tagatose.

(b) Draw the most stable conformation of the most stable cyclic hemiacetal form of tagatose.

Question. (a) Figure 23-2 shows that the degradation of D-glucose gives D-arabinose, an aldopentose. Arabinose is most stable in its furanose form. Draw D-arabinofuranose.

(b) Ribose, the C2 epimer of arabinose, is most stable in its furanose form. Draw D-ribofuranose.

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