Concept:
Carbohydrates and amino acids have characteristic functional group compositions and oxidation states that can be recognized by their chemical structures and Fischer projection formulas. Step 1: Identifying Gluconic Acid (A):
Gluconic acid is a monocarboxylic aldonic acid formed by mild oxidation of the aldehyde group of D-glucose using bromine water:
\[
\text{HOCH}_2-(\text{CHOH})_4-\text{CHO} \xrightarrow{\text{Br}_2/\text{H}_2\text{O}} \text{HOCH}_2-(\text{CHOH})_4-\text{COOH}
\]
Structure (III) shows a six-carbon chain containing one terminal carboxyl group (\(-\text{COOH}\)) at C1 and a primary alcohol group (\(-\text{CH}_2\text{OH}\)) at C6.
Therefore, (A) matches with (III). Step 2: Identifying Fructose (B):
D-Fructose is a ketohexose with the structure \(\text{HOCH}_2-\text{CO}-(\text{CHOH})_3-\text{CH}_2\text{OH}\).
Structure (IV) depicts a six-carbon ketose chain with a ketone carbonyl group at C2 and primary alcohol groups at both ends (C1 and C6).
Therefore, (B) matches with (IV). Step 3: Identifying Tryptophan (C):
Tryptophan is an essential \(\alpha\)-amino acid containing an aromatic indole heterocyclic side chain attached to the \(\beta\)-carbon of alanine.
Structure (II) shows an amino acid containing an indole bicyclic system:
\[
\text{Indole}-\text{CH}_2-\text{CH}(\text{NH}_2)-\text{COOH}
\]
Therefore, (C) matches with (II). Step 4: Identifying Saccharic Acid (D):
Saccharic acid (glucaric acid) is a dicarboxylic aldaric acid formed by strong oxidation of both the C1 aldehyde and C6 primary alcohol groups of D-glucose with concentrated nitric acid:
\[
\text{HOOC}-(\text{CHOH})_4-\text{COOH}
\]
Structure (I) shows a six-carbon chain terminated by two carboxylic acid groups (\(-\text{COOH}\)) at positions C1 and C6.
Therefore, (D) matches with (I). Final Answer:
The correct matching sequence is (A)-(III), (B)-(IV), (C)-(II), (D)-(I), corresponding to option (D).
