課程名稱︰生物有機化學 課程性質︰必修 課程教師︰方俊民 開課學院： 開課系所︰ 考試日期（年月日）︰2015/10/20 考試時限（分鐘）：110 試題 : I.(6%) Describe at least three biological functions of carbonhydrates, and give at least one example for each function. II.(9%)The reaction of aldehyde with alcohol forms acetal via an intermediate of hemiacetal. Ｏ + + ∥ H H OR' H , R'OH H OR' ╱╲ + R'OH ←→ ╳ ←———→ ╳ + H O R　　H R OH R OR' 2 ／╲ ＿ ＿ ∣ ∣ H ╱ ╲ H ╱ ╲ H ／ ╲╱ ∣ ▕／ ∣ ▕／ HO ∥ ╲ ╱＼ ╲ ╱＼ Ｏ Ｏ OH Ｏ OCH 3 (A) (B) (C) 1. Describe the relationship between the structures of A and B. 2. What is the product for the reaction of compound B with NaBH . 4 3. How will you prepare compound C from compound A? III.(45%) The molecular formula of glucose is HOCH CH(OH)CH(OH)CH(OH)CH(OH)CHO, and fructose is 2 HOCH CH(OH)CH(OH)CH(OH)CH(=O)CH OH. 2 2 1. Indicate the position of carbonyl group in glucose. 2. Indicate which carbon containing a primary hydroxyl group in glucose. 3. One can classify fructose as a __(A)__ by the number of carbons, and as a __(B)__ by its main functional group. 4. What is the product for reaction of glucose with Tollens' reagent? (AgNO /NH OH) 3 4 5. Draw the structure of D-glucose in Fischer projection. 6. Which carbon certer is responsible for the definition of D-sugar? 7. Does C-3 in D-glucose have R or S configuration? 8. On treatment in aqueous NaOH solution, D-glucose can be converted to D-fructose via a dienolate ion. Show the reaction mechanism. 9. Draw the cyclic structure of β-D-glucopyranose in chair configuration. 10.β-D-glucopyranose and α-D-glucopyranose are isomers that are specifically called __(C)__ because they are cyclic stereoisomers having different configurations at the hemiacetal center. 11.Show the mechanism for the interconversion between β-D-glucopyranose and α-D-glucopyranose in water. 12.What is the product for reaction of β-D-glucopyranose with acetic anhydride in the presence of a base pyridine? 13.Draw the cyclic structure of D-fructofuranose. 14.Maltose is a disaccharide Glc(α1→4)Glc formed by two D-glucose molecules. Draw the structure of maltose. 15.Indicate the acetal and hemiacetal groups in maltose. IV.(42%)Compounds 1-7 are common L-amino acids. NH _ NH ＣOOH HOOC = 2 ／ ╲﹍H = 2 H N┼H ＼／＼ ╲ ／╲ ／＼／＼／＼ 2 ＣH COOH N COOH H N COOH 3 | 2 H (1) (2) (3) (4) H N ＮH Ｈ 2 ＼∥ Ｎ ∣ NH __╱ ╲ NH Ｎ＿ NH Ｎ = 2 // \\__// = 2 // \\ = 2 ／ ＼／＼／＼ ∣ ∣ ＼／＼ ╲ ╱╲╱╲ H COOH \\__// COOH Ｎ COOH Ｈ (5) (6) (7) 1. Draw the zwitterionic form of compound 1. 2. Which compound __(A)__ contains secondary amino group? 3. Which COOH in compound 2 has lower pKa value? 4. Which compound __(B)__ contains the most basic group? 5. Which compound __(C)__ contains a chromophore with absorption at λ =280nm max 6. Which compound __(D)__ has an imidazole group to act as both general acid and general base? 7. For compound 1: which group __(E)__ is responsible for pKa1=2.34? which group __(F)__ is responsible for pKa2=9.69? what is the value __(G)__ of its isoelectric point (pI)? 8. Which compound __(H)__ has the isoelectric point close to physiological pH? 9. Describe how to separate compounds 1, 2 and 4 by electrophoresis. 10.Draw the structures of two dipeptides contstructed by amino acid 1 and 3. 11.Explain why peptide bond is rather rigid that cannot rotate freely at room termperature. --

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