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    3 Amino Acids

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    rlznrecur
    The document discusses amino acids and proteins. It introduces the 20 standard amino acids that make up proteins, describing their general chemical structure including the central alpha carbon and the different R groups that determine each amino acid's properties. The document also discusses the chirality of amino acids, the different types based on their R groups including hydrophobic, polar uncharged, and charged amino acids. It covers the ionization states of amino acids and how they are affected by pH. Finally, it briefly outlines some non-protein functions of amino acids and identifies the 9 essential amino acids humans must obtain through their diet.

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    3 Amino Acids

    Uploaded by

    rlznrecur
    100 views25 pages
    The document discusses amino acids and proteins. It introduces the 20 standard amino acids that make up proteins, describing their general chemical structure including the central alpha carbon and the different R groups that determine each amino acid's properties. The document also discusses the chirality of amino acids, the different types based on their R groups including hydrophobic, polar uncharged, and charged amino acids. It covers the ionization states of amino acids and how they are affected by pH. Finally, it briefly outlines some non-protein functions of amino acids and identifies the 9 essential amino acids humans must obtain through their diet.

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    The document discusses amino acids and proteins. It introduces the 20 standard amino acids that make up proteins, describing their general chemical structure including the central alpha carbon and the different R groups that determine each amino acid's properties. The document also discusses the chirality of amino acids, the different types based on their R groups including hydrophobic, polar uncharged, and charged amino acids. It covers the ionization states of amino acids and how they are affected by pH. Finally, it briefly outlines some non-protein functions of amino acids and identifies the 9 essential amino acids humans must obtain through their diet.

    Copyright:

    Attribution Non-Commercial (BY-NC)
    Download as PDF, TXT or read online from Scribd
    Download as pdf or txt
    100 views25 pages

    3 Amino Acids

    Uploaded by

    rlznrecur
    The document discusses amino acids and proteins. It introduces the 20 standard amino acids that make up proteins, describing their general chemical structure including the central alpha carbon and the different R groups that determine each amino acid's properties. The document also discusses the chirality of amino acids, the different types based on their R groups including hydrophobic, polar uncharged, and charged amino acids. It covers the ionization states of amino acids and how they are affected by pH. Finally, it briefly outlines some non-protein functions of amino acids and identifies the 9 essential amino acids humans must obtain through their diet.

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    Lecture 3: Amino Acids

    • Friday, January 14 th

    • Reading assignment: Chapter 3


    • Overview
    - introduction to protein function
    - chemical structure of amino acids; chirality
    - types of amino acids: non-polar, polar uncharged, charged
    - ionization of amino acids
    - peptide bonds
    Protein Terminology

    • Proteins are made up of one or more polypeptides


    - polymers of amino acids
    - linked by peptide bonds
    • Polypeptides of fewer than 50 amino acids are called
    “peptides”
    • Some proteins also contain non-amino acid parts called
    “prosthetic groups”
    - covalently or noncovalently bound to polypeptide
    Protein Populations

    • Number of possible proteins in an organism:


    - determined by the number of genes
    • E. coli: 6000
    • yeast: 12,000
    • humans: 25,000
    • plants: 25,000
    • Number of proteins per cell
    - subsets from the total possible
    - approximately 5,000 in eukaryotic cells
    • Differential gene expression
    - expression of a gene results in presence of a polypeptide
    Protein Functions

    • Structural proteins
    - cell architecture
    - physical movements
    • Transporters and carriers of small molecules
    - passage across membranes
    • Enzymes - reaction catalysts
    • Protection
    - antibodies or toxins
    - detoxification
    • Signal detection and transmission
    • Nitrogen storage
    Amino Acid Structure (i)

    • Twenty different amino acids in proteins


    - these are the standard amino acids
    • General structure
    - central α carbon (usually chiral) bound to:
    • amino group
    • carboxylic acid group
    • hydrogen atom
    • one of 20 different R groups
    • R group chemical properties vary
    • Amino and carboxyl groups are ions at pH 7
    Amino Acid Structure (ii)
    Amino Acid Chirality

    • Four different constituents on α carbon


    - enantiomers
    • referred to as D and L
    - glycine is exception because R group is a second hydrogen
    • Almost all amino acids in biomolecules are L
    Amino Acid
    Chirality
    R-group Properties: Hydrophobic

    • Non-polar (hydrophobic)
    - neutral at pH 7
    - aliphatic
    • glycine, alanine, valine, leucine, isoleucine, proline, methionine
    - aromatic
    • phenylalanine,
    tryptophan
    R-group Properties: Hydrophobic
    R-group Properties: Hydrophobic
    R-group Properties: Polar, Uncharged, Hydrophilic

    • Neutral at pH 7
    - aliphatic
    • threonine, serine, asparagine, glutamine, cysteine
    - aromatic
    • tyrosine
    R-group Properties: Polar, Uncharged, Hydrophilic
    R-group Properties: Charged, Hydrophilic

    • Negative at pH 7 (acidic)
    - aspartate, glutamate
    R-group Properties: Charged, Hydrophilic

    • Positive at pH 7 (acidic)
    - lysine, arginine, histidine
    - histidine is special case
    • can be positive
    or neutral
    Ionization Of Amino Acids

    • Amino acids two or three ionizable groups


    - both an acid and a base
    • acid: the α carboxyl group; pK = ~2
    a

    • base: the α amino group; pK = ~9.5


    a

    • zwitterions at pH 7
    • Some R groups also can accept or donate H+
    - acids
    • Asp, Glu
    - bases
    • Lys, Arg, His
    Ionization Of Amino and Carboxyl Groups
    Ionization Of Amino Acids
    Ionic States of Aspartic Acid

    high pH, low [H+],


    fully dissociated

    low pH, high [H+],


    fully protonated
    pKa for Functional Groups in Proteins
    pKa for Functional Groups in Proteins
    Titration Of Amino Acids

    • Two or three inflection points


    • Isoelectric point (pI)
    - pH at which the net charge is 0
    Ionization of Histidine

    • pKa of the imidizole nitrogen near physiological pH


    • Both protonated and dissociated form can be present in
    significant proportions
    - they can convert back and forth
    - important as a proton acceptor/donor in many catalytic mechanisms
    Non-protein Functions of Amino Acids

    • Metabolic intermediates used to produce:


    - neurotransmitters:
    • GABA, serotonin
    - synthesis of nucleic acid bases, heme,
    chlorophyll
    - nitrogen excretion cycle
    • citrulline, ornithine
    - hormones
    • indole acetic acid
    Essential Amino Acids

    • Nine amino acids cannot be synthesized by humans


    - must be acquired in the diet

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