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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

Without referring to the chapter, draw the chair conformation of

(a) α -D-mannopyranose (the C2 epimer of glucose).

(b) β -D-allopyranose (the C3 epimer of glucose.)

(c) α -D-galactopyranose (the C4 epimer of glucose).

(d) N-formylglucosamine, glucose with C2 oxygen atom replaced by a formylated amino group.

Treatment of either anomer of fructose with excess ethanol in the presence of a trace of HCI gives a mixture of the α and β anomers of ethyl-D-fructofuranoside. Draw the starting materials, reagents, and products for this reaction. Circle the aglycone in each product.

Question. Retroviruses like HIV, the pathogen responsible for AIDS, incorporate an RNA template that is copied into DNA during infection. The reverse transcriptaseenzyme that copies RNA into DNA is relatively nonselective and error-prone, leading to a high mutation rate. Its lack of selectivity is exploited by the anti-HIV drug AZT (3’-azido-2’,3’-dideoxythymidine), which becomes phosphorylated and is incorporated by reverse transcriptase into DNA, where it acts as a chain terminator. Mammalian DNA polymerases are more selective, having a low affinity for AZT, so its toxicity is relatively low.

  1. Draw the structures of AZT and natural deoxythymidine.
  2. Draw the structure of AZT 5’-triphosphate, the derivative that inhibits reverse transcriptase.

Ruff degradation of D-arabinose gives D-erythrose. The Kiliani-Fischer synthesis converts D-erythrose to a mixture of D-arabinose and D-ribose. Draw out these reactions and give the structure of D-ribose.

Like glucose, galactose mutarotates when it dissolves in water. The specific rotation of α-D-galactopyranoseis +150.70 , and that of the β anomer is +52.80 . When either of the pure anomers dissolves in water, the specific rotation gradually changes to +80.20. Determine the percentages of the two anomers present at equilibrium.
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