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Chapter 23: Q36P (page 1236)

Draw the structure of the individual mutarotating α and β anomers of maltose.

Short Answer

Expert verified

Draw the structure of the individual mutarotating α and β anomers of maltose.

Step by step solution

01

A concept:

Maltose is a disaccharide which is obtained as a result of partial hydrolysis of starch by an enzyme known as diastase.

Hydrolysis of maltose in presence of dilute acids yields only D-glucose which implies that the maltose molecule is made up of two glucose units. Two glucose units in maltose are linked by an α glycosidic linkage between C1 of one unit and C4 of another unit. Maltose is known to exist both in α and β forms, each of which exhibits mutarotation.

02

Draw the structure:

The structures of α and β anomers of maltose are shown below:

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Most popular questions from this chapter

(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.

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

(a) Show the product that results when fructose is treated with an excess of methyl iodide and silver oxide.

(b) Show what happens when the product of part (a) is hydrolyzed using dilute acid.

(c) What do the results of parts (a) and (b) imply about the hemiacetal structure of fructose?

. (a) An aliphatic aminoglycoside is relatively stable to base, but it is quickly hydrolyzed by dilute acid. Propose a mechanism for the acid-catalyzed hydrolysis.

(b) Ribonucleosides are not so easily hydrolyzed, requiring relatively strong acid. Using your mechanism for part (a), show why cytidine and adenosine (for example) are not so readily hydrolyzed. Explain why this stability is important for living organisms.

(a) Which of the D-aldopentoses will give optically active aldaric acids on oxidation with HNO3 ?

(b) Which of the D-aldotetroses will give optically active aldaric acids on oxidation withHNO3 ?

(c) Sugar X is known to be a D-aldohexose. On oxidation with HNO3 , X gives an optically inactive aldaric acid. When X is degraded to an aldopentose, oxidation of the aldopentose gives an optically active aldaric acid. Determine the structure of X.

(d) Even though sugar X gives an optically inactive aldaric acid, the pentose formed by degradation gives an optically active aldaric acid. Does this finding contradict the principle that optically inactive reagents cannot form optically active products?

(e) Show what products results if the aldopentose formed from degradation of X is further degraded to an aldotetrose. DoesHNO3 oxidize this aldotetrose to an optically active aldaric acid?
See all solutions

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