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Amines

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1. Amines. Organic compounds of nitrogen N. Classified as primary, ... Contractile muscles. Transport hemoglobin. Storage milk. Hormonal insulin, growth hormone ... – PowerPoint PPT presentation

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Title: Amines


1
Amines
  • Organic compounds of nitrogen N
  • Classified as primary, secondary, tertiary
  • CH3 CH3
  • ? ?
  • CH3NH2 CH3NH CH3N CH3
  • 1 2 3

2
Naming Amines
  • IUPAC aminoalkane Common alkylamine
  • CH3CH2NH2 CH3NH CH3
  • aminoethane N-methylaminomethane
  • (ethylamine) (dimethylamine)
  • NH2
  • CH3CHCH3
  • 2-aminopropane Aniline N-methylaniline
  • (isopropylamine)

3
Amides
  • Derivatives of carboxylic acids where an amino
    (-NH2) group replaces the OH group.
  • O O
  • ?? ??
  • CH3 COH CH3 CNH2
  • carboxylic acid amide
  • acetic acid acetamide

4
Naming Amides
  • Alkanamide from acid name
  • O
  • ?? methanamide (IUPAC)
  • HCNH2 formamide (common)
  • O
  • ?? propanamide (IUPAC)
  • CH3CH2CNH2 propionamide(common)

5
Naming Amides with N-Groups
  • O
  • ??
  • CH3CNHCH3 N-methylethanamide (IUPAC)
  • N-methylacetamide (common)
  • O
  • ??
  • CH3CH2CN(CH3)2
  • N,N-dimethylpropanamide
  • N,N-dimethylpropionamide

6
Amino Acids Proteins, and Enzymes
  • Types of Proteins
  • Amino Acids
  • The Peptide Bond

7
Types of Proteins
  • Type Examples
  • Structural tendons, cartilage, hair, nails
  • Contractile muscles
  • Transport hemoglobin
  • Storage milk
  • Hormonal insulin, growth hormone
  • Enzyme catalyzes reactions in cells
  • Protection immune response

8
Amino Acids
  • Building blocks of proteins
  • Carboxylic acid group
  • Amino group
  • Side group R gives unique characteristics
  • R side chain
  • I
  • H2NC COOH
  • I
  • H

9
Examples of Amino Acids
  • H
  • I
  • H2NC COOH
  • I
  • H glycine
  • CH3
  • I
  • H2NC COOH
  • I
  • H alanine

10
Types of Amino Acids
  • Nonpolar R H, CH3, alkyl groups, aromatic
  • O
  • Polar ll
  • R CH2OH, CH2SH, CH2CNH2,
  • (polar groups with O-, -SH, -N-)
  • Polar/Acidic
  • R CH2COOH, or -COOH
  • Polar/ Basic
  • R CH2CH2NH2

11
Nonpolar R groups
12
Polar R groups.
13
Polar R groups
14
Learning Check AA1
  • Identify each as (1) polar or (2) nonpolar
  • A. NH2CH2COOH (Glycine)
  • CH3
  • CHOH
  • B. NH2CHCOOH (Serine)

15
Solution AA1
  • Identify each as (1) polar or (2) nonpolar
  • A.(2) NH2CH2COOH (Glycine)
  • CH3
  • CHOH
  • B. (1) NH2CHCOOH (Serine)

16
Essential Amino Acids
  • 10 amino acids not synthesized by the body
  • arg, his, ile, leu, lys, met, phe, thr, trp, val
  • Must obtain from the diet
  • All in diary products
  • 1 or more missing in grains
  • and vegetables

17
Amino Acids as Acids and Bases
  • Ionization of the NH2 and the COOH group
  • Zwitterion has both a and charge
  • Zwitterion is neutral overall
  • NH2CH2COOH H3NCH2COO
  • glycine Zwitterion of glycine

18
pH and ionization
  • H OH
  • H3NCH2COOH H3NCH2COO H2NCH2COO
  • Positive ion zwitterion Negative ion
  • Low pH neutral pH High pH

19
Learning Check AA2
  • CH3 CH3
  • H3NCHCOOH H2NCH2COO
  • (1) (2)
  • Select from the above structures
  • A. Alanine in base.
  • B. Alanine in acid.

20
Solution AA2
  • CH3 CH3
  • H3NCHCOOH H2NCH2COO
  • (1) (2)
  • Select from the above structures
  • (2) Alanine in base.
  • (1) Alanine in acid.

21
The Peptide Bond
  • Amide bond formed by the COOH of an amino acid
    and the NH2 of the next amino acid
  • O CH3
  • NH3CH2CO H3NCHCOO
  • O CH3
  • NH3CH2C NCHCOO
  • peptide bond
  • H

22
Naming Amides with N-Groups
  • O
  • ??
  • CH3CNHCH3 N-methylethanamide (IUPAC)
  • N-methylacetamide (common)
  • O
  • ??
  • CH3CH2CN(CH3)2
  • N,N-dimethylpropanamide
  • N,N-dimethylpropionamide

23
Peptides
  • Amino acids linked by amide (peptide) bonds
  • Gly Lys Phe Arg
    Ser
  • H2N- -COOH
  • end Peptide bonds end
  • Glycyllysylphenylalanylarginylserine

24
Learning Check AA3
  • What are the possible tripeptides formed from
    one each of leucine, glycine, and alanine?

25
Solution AA3
  • Tripeptides possible from one each of leucine,
    glycine, and alanine
  • Leu-Gly-Ala
  • Leu-Ala-Gly
  • Ala-Leu-Gly
  • Ala-Gly-Leu
  • Gly-Ala-Leu
  • Gly-Leu-Ala

26
Learning Check AA4
  • Write the three-letter abbreviations for the
    following tetrapeptide

27
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28
Solution AA4
  • Ala-Leu-Cys-Met

29
Primary Structure of Proteins
  • The particular sequence of amino acids that is
    the backbone of a peptide chain or protein

Ala-Leu-Cys-Met
30
Secondary Structure Alpha Helix
  • Three-dimensional arrangement of amino acids with
    the polypeptide chain in a corkscrew shape
  • Held by H bonds between the H of N-H group and
    the O of CO of the fourth amino acid along the
    chain
  • Looks like a coiled telephone cord

31
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32
Secondary Structure Beta Pleated Sheet
  • Polypeptide chains are arranged side by side
  • Hydrogen bonds form between chains
  • R groups of extend above and below the sheet
  • Typical of fibrous proteins such as silk

33
Pleated sheet
34
Secondary Structure Triple Helix
  • Three polypeptide chains woven together
  • Glycine, proline, hydroxy proline and
    hydroxylysine
  • H bonding between OH groups gives a strong
    structure
  • Typical of collagen, connective tissue, skin,
    tendons, and cartilage

35
Collagen and pleated sheet
36
Tertiary Structure
  • Specific overall shape of a protein
  • Cross links between R groups of amino acids in
    chain
  • disulfide SS
  • ionic COO H3N
  • H bonds CO HO
  • hydrophobic CH3 H3C

37
Stabilizing protein
38
Learning Check P2
  • Select the type of tertiary interaction as
  • (1) disulfide (2) ionic
  • (3) H bonds (4) hydrophobic
  • A. Leucine and valine
  • B. Two cysteines
  • C. Aspartic acid and lysine
  • Serine and threonine

39
Leucine and Valine
40
Two Cysteines
41
Aspartic Acid and Lysine
42
Serine and Threonine
43
Solution P2
  • Select the type of tertiary interaction as
  • (1) disulfide (2) ionic
  • (3) H bonds (4) hydrophobic
  • A. 4 Leucine and valine
  • B. 1 Two cysteines
  • C. 2 Aspartic acid and lysine
  • 3 Serine and threonine

44
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