Amino acids: Structure General chemical properties

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Presentation transcript:

Amino acids: Structure General chemical properties CHMI 2227E Biochemistry I Amino acids: Structure General chemical properties CHMI 2227 - E.R. Gauthier, Ph.D.

Proteins: Building blocks of life! CHMI 2227 - E.R. Gauthier, Ph.D.

Amino acids C H R COOH NH2 Ca CHMI 2227 - E.R. Gauthier, Ph.D.

General properties of amino acids. CHMI 2227 - E.R. Gauthier, Ph.D.

General properties of amino acids. Zwitterion Net charge: +1 Net charge: 0 Net charge: -1 Acidic pH Basic pH pKa 1 (pH 2-2.5) pKa 2 (pH 9-10.5) CHMI 2227 - E.R. Gauthier, Ph.D.

Amino acid titration 1. simplest scenario Buffer! CHMI 2227 - E.R. Gauthier, Ph.D.

The twenty amino acids: CHMI 2227 - E.R. Gauthier, Ph.D.

Structure of the 20 amino acids 1. Hydrophobic amino acids CHMI 2227 - E.R. Gauthier, Ph.D.

Structure of the 20 amino acids 1. Hydrophobic amino acids CHMI 2227 - E.R. Gauthier, Ph.D.

Structure of the 20 amino acids 2. Aromatic amino acids CHMI 2227 - E.R. Gauthier, Ph.D.

Structure of the 20 amino acids 2. Aromatic amino acids Absorbance max (nm) Molar (M-1 cm-1) Phenylalanine 257.4 197 Tyrosine 274.6 1420 Tryptophan 279.8 5690 CHMI 2227 - E.R. Gauthier, Ph.D.

Structure of the 20 amino acids 3. polar, uncharged amino acids CHMI 2227 - E.R. Gauthier, Ph.D.

Structure of the 20 amino acids Cysteine and cystine Disulfide bond In biochem: oxidation: lose H Reduction: gain H CHMI 2227 - E.R. Gauthier, Ph.D.

Structure of the 20 amino acids Tyr, Ser, Thr P=O O- Ser Phospho-Ser Protein kinase phosphatase ATP ADP H2O PO4-3 CHMI 2227 - E.R. Gauthier, Ph.D.

Structure of the 20 amino acids 4. Negatively charged amino acids CHMI 2227 - E.R. Gauthier, Ph.D.

Structure of the 20 amino acids 4. Negatively charged amino acids pKa1 pKa2 pKaR What is the pI of glutamate? NaOH pH 9.5 4.1 2.1 100% A 100% B 100% C 100% D A B C D CHMI 2227 - E.R. Gauthier, Ph.D.

Structure of the 20 amino acids 5. Positively charged amino acids CHMI 2227 - E.R. Gauthier, Ph.D.

Structure of the 20 amino acids 5. Positively charged amino acids: His pKaR pKa2 CHMI 2227 - E.R. Gauthier, Ph.D.

Structure of the 20 amino acids pKa values of amino acids CHMI 2227 - E.R. Gauthier, Ph.D.

Analysis of amino acids 1. Ion exchange chromatography Elution + pH >> pI pH << pI CHMI 2227 - E.R. Gauthier, Ph.D.

Analysis of amino acids 2. Detection of amino acids: ninhydrin reagent OH Ninhydrin Amino acid 2 N C H R COO- NH3+ CO2 Purple!! R-HC=O CHMI 2227 - E.R. Gauthier, Ph.D.