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Resonance Stability of the

Peptide Bond
Peptide Bond

• Has Double-Bond characteristics

• makes the peptide bond planar
• prevents rotation around the peptide bond
Directionality
From N-terminal to Carboxyl Terminal
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Geometric Isomerism of the

Modified Amino Acids
Peptide Bond

trans cis

cis isomers have higher steric strain, thus, they are not favored
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Modified Amino Acids Modified Amino Acids

Acetyl Groups Hydroxyl Groups
• Adding to the N-terminal makes the protein more resistant to • Converting proline to hydroxyproline stabilizes the fibers of
degradation the collagen.
• Scurvy, a deficiency of Vitamin C, leads to inability to produce
hydroxyproline in collagen. This results to a decrease in tissue
strength

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Modified Amino Acids Modified Amino Acids

Carboxyl Groups Carbohydrate Units
• In Vitamin K deficiency, insufficient carboxylation of glutamate • Sugars attached to asparginine units of
residue in prothrombin, a clotting protein, leads to protein makes it more hydrophilic and
hemorrhage enable it to interact with other proteins.

Fatty acid Units

• Makes the group more hydrophilic

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