Exam 23: Carbohydrates and Nucleic Acids

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Given the structure of D-altrose below, draw the structure of L-altrose. Given the structure of D-altrose below, draw the structure of L-altrose.

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When D-(+)-xylose is treated with nitric acid, which of the following results?

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C

Stereoisomeric aldohexoses that differ in configuration at only a single carbon are:

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E

Provide the structure of the open-chain form of L-altrose.

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Provide the structure of adenosine monophosphate.

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What is the major structural difference between a ribonucleoside and a ribonucleotide?

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Draw the Haworth structure of the β-pyranose form of the monosaccharide shown below. Draw the Haworth structure of the β-pyranose form of the monosaccharide shown below.

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Draw the Fischer projection of (2S,3R)-2,3-dihydroxybutanoic acid, and label it as erythro or threo.

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Draw the Haworth structure of β-D-glucopyranose.

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What nucleophilic carbon species is used in the Kiliani-Fischer synthesis?

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Draw the Haworth structure of the α-furanose form of the monosaccharide shown below. Draw the Haworth structure of the α-furanose form of the monosaccharide shown below.

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How many asymmetric centers are present in the open chain form of the aldohexose D-(-)-gulose?

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Fructose forms:

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Draw the Haworth structure of the β-furanose form of the monosaccharide shown below. Draw the Haworth structure of the β-furanose form of the monosaccharide shown below.

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An optically active D-aldopentose produced an optically inactive alditol upon treatment with NaBH4. When this aldopentose was subjected to a Ruff degradation, a D-aldotetrose was generated. This aldotetrose gave an optically active aldaric acid upon oxidation with HNO3. Use these data to provide the structure of the starting D-aldopentose.

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Draw the Fischer projection of the open chain form of D-arabinose.

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Provide the structure of guanosine.

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Alpha-D-Glucopyranose will chemically react with t-butanol (aglycone) under acidic conditions in the formation of a glycoside. Show the structure of the final product of this reaction in the chair conformation.

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Most monosaccharides are highly water soluble. Offer an explanation.

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Name the two purine bases which serve as components in ribonucleosides.

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