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Use fig. 23-3 (the D-family of aldoses) to name the following aldoses.

(a) The C2 epimer of D-xylose

(b) The C3 epimer of D-erythrose

(c) The C3 epimer of D-altros

(d) The enantiomer of D-talose

(e) The C-5 epimer of D-idose

Short Answer

Expert verified

(a) The C2 epimer of D-xylose:

(b) The C3 epimer of D-erythrose

(c) The C3 epimer of D-altros

(d) The enantiomer of D-talose:

(e) The C-5 epimer of D-idose:

Step by step solution

01

(a) The C2 epimer of D-xylose:  

C2 epimer of D-xylose is D-lyxose:

02

(b) The C3 epimer of D-erythrose:

C3 epimer of D-erythrose is L-Threose:

03

(c) The C3 epimer of D-altros:

C3 epimer of D-altros is D-mannose:

04

(d) The enantiomer of D-talose:

The enantiomer of D-talose is L-talose

05

(e) The C-5 epimer of D-idose:

The C-5 epimer of D-idose is L-glucose:

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Most popular questions from this chapter

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.

The carbonyl group in D-galactose may be isomerized from C1 to C2 by brief treatment with dilute base (by enediol rearrangement, Section 23-7). The product is the C4 epimer of fructose. Draw the furanose structure of the product.

Aldohexoses A and B both undergo Ruff degradation to give aldopentose C. On treatment with warm nitric acid, aldopentose C gives an optically active aldaric acid. B also reacts with warm nitric acid to give an optically active aldaric acid, but A reacts to give an optically inactive aldaric acid. Aldopentose C is degraded to aldotetrose D, which gives optically active tartaric acid when it is treated with nitric acid. Aldotetrose D is degraded to (+)-glyceraldehyde. Deduce the structures of sugars A,B,C and D, and use Figure 23-3 to determine the correct names of these sugars.

Show the products that result from hydrolysis of amygdalin in dilute acid. Can you suggest why amygdalin might be toxic to tumor (and possibly other) cells?

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.
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