Identify the pair of reactants that upon reaction, with elimination of HCl will give rise to the dipeptide Gly-Ala.
- NH2-CH2-COOH and NH2- CH3 |CH-COOH
- NH2-CH2-COCl and NH3- CH3 |CH-COCl
- NH2-CH2-COCl and NH2- CH3 |CH-COOH
- NH2-CH2-COOH and NH2- CH3 |CH-COCl
Answer
(3) NH2-CH2-COCl and NH2- CH3 |CH-COOH
Solution
In the dipeptide Gly-Ala, the –CO– of glycine is joined to the –NH– of alanine (N-terminal residue written first):
NH2-CH2-CO-NH- CH3 |CH-COOH
To form this amide bond with loss of HCl, glycine must react as its acid chloride and alanine through its free -NH2 group:
NH2-CH2-COCl + NH2- CH3 |CH-COOH
NH2-CH2-CO-NH- CH3 |CH-COOH + HCl
(A) would need loss of water, not HCl. (D) loses HCl but joins the –CO– of alanine to the –NH– of glycine, giving Ala-Gly. In (B) the - NH3 group has no lone pair to attack.
Answer: (3)