15 Survey of Biomolecules-Amino Acids, Peptides and Proteins

Organic Chemistry: Structure and Function

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1 Survey of Biomolecules Part III: Amino Acids, Peptides, and Proteins Lecture Supplement: Take one handout from the stage
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2 Why Bother With Protein Structure? Structure controls function Enzyme selectivity Drug design Many others Fundamental protein structure = amide polymer N H O H R n Repeating unit N H O N H R N H O N H R H H R O O H H R
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3 asic building block of protein structure = amino acid All have amine and carboxylic acid groups All are primary amines (-NH 2 ) except proline Side chains attached to α -carbon vary Most have S configuration at α -carbon, except glycine (R = H) Amine + carboxylic acid = proton transfer possible Amino Acids K eq > 1 at physiological pH Neutral (unionized) form Zwitterionic (ionized) form α -carbon N H O H R OH H N O H R H H H
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4 Amino Acids he 21 natural amino acids categorized by side chain properties: Hydrophilic versus hydrophobic ydrophobic nonacidic side chains Glycine (Gly) Achiral Alanine (Ala) Valine (Val) Leucine (Leu) Isoleucine (Ile) Proline (Pro) 2 o amine (HNR 2 ) Tryptophan (Try) Phenylalanine (Phe) Methionine (Met) H 2 N COOH H H Acidic versus basic versus neither (nonacidic) H 2 N COOH H H 3 C H 2 N COOH H H 2 N COOH H H 2 N COOH H COOH N H H H 2 N COOH H HN H 2 N COOH H H 2 N COOH H CH 3 S
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5 Amino Acids Hydrophobic acidic side chains Cysteine (Cys) Selenocysteine (Sec) Rare Hydrophilic nonacidic side chains Serine (Ser) Threonine (Thr)
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15 Survey of Biomolecules-Amino Acids, Peptides and...

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