☰ Contents · Chemistry (Organic chemistry)

Amino acids and proteins

Lessons 34 · 1 lessons · A. Mutalibov, E. Murodov, S. Masharipov, H. Islomova. Organic Chemistry, Grade 10, 1st edition. G‘afur G‘ulom Publishing House, Tashkent, 2017
34

Amino acids and proteins: preparation and properties

Textbook: pp. 139–145
GoalExplain the amphoteric properties of amino acids, the peptide bond and the structure, properties and qualitative tests of proteins.
New words
amino acid · aminokislotaamphoteric character · amfoterlikpeptide bond · peptid bog‘protein · oqsil (protein)
Explanation

Compounds that contain both an amino group –NH₂ and a carboxyl group –COOH are amino acids; the general formula is H₂N–CH(R)–COOH. The simplest are glycine H₂N–CH₂–COOH (aminoethanoic acid) and alanine CH₃–CH(NH₂)–COOH. Having two groups, they are amphoteric: they react with acids (H₂N–CH₂–COOH + HCl → ClH₃N–CH₂–COOH) and with alkalis (H₂N–CH₂–COOH + NaOH → H₂N–CH₂–COONa + H₂O) and form esters with alcohols. When two amino acids join, water is lost between the –COOH of one and the –NH₂ of the other, forming a peptide bond –CO–NH–: glycine + alanine → dipeptide + H₂O; this is polycondensation. Many amino acid residues make up proteins; natural proteins are built from about 20 α-amino acids, some of which the body cannot synthesize and must obtain from food (essential amino acids). Proteins act as enzymes, building material, antibodies and more. Hydrolysis breaks a protein down into amino acids. Heating, strong acid, alkali and heavy-metal salts denature a protein. Qualitative tests: the biuret test (violet colour with alkali and a little copper(II) sulfate) and the xanthoprotein test (yellow with concentrated HNO₃).

Worked examples
If glycine C₂H₅NO₂ (75 g/mol) and alanine C₃H₇NO₂ (89 g/mol) form a dipeptide, M = 75 + 89 − 18 = 146 g/mol. A tripeptide made of three amino acids has 2 peptide bonds.
75 g of glycine (1 mol) with NaOH gives 1 mol of sodium glycinate (H₂N–CH₂–COONa, M = 97), i.e. 97 g of salt. A linear polypeptide of 50 residues has 49 peptide bonds.
Class activity

In class the teacher shows the biuret test on egg white (dilute alkali and a little CuSO₄ solution); record the colour change. Chemicals stay in the teacher’s hands; no independent testing is done.

Practice
1
Write the general formula of an amino acid.
2
What is the molar mass of the dipeptide of glycine (75) and alanine (89)?
3
How many grams of sodium glycinate (M = 97) form when 75 g of glycine (M = 75) react with NaOH?
4
Why are amino acids amphoteric?