Amino Acids. Dr. Kevin Ahern

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1 Amino Acids Dr. Kevin Ahern

2 Part 1 - Amino Acids Structure and Chemistry

3 Part 1 - Amino Acids Structure and Chemistry Building Blocks of Proteins

4 Part 1 - Amino Acids Structure and Chemistry Building Blocks of Proteins Essential Amino Acids

5 Part 1 - Amino Acids Structure and Chemistry Building Blocks of Proteins Essential Amino Acids Basic Structure

6 Part 1 - Amino Acids Structure and Chemistry Building Blocks of Proteins Essential Amino Acids Basic Structure Stereochemistry

7 Part 1 - Amino Acids Structure and Chemistry Building Blocks of Proteins Essential Amino Acids Basic Structure Stereochemistry Side Chain Chemistry

8 Part 1 - Amino Acids Structure and Chemistry Building Blocks of Proteins Essential Amino Acids Basic Structure Stereochemistry Side Chain Chemistry Properties

9 Part 1 - Amino Acids Structure and Chemistry Building Blocks of Proteins Essential Amino Acids Basic Structure Stereochemistry Side Chain Chemistry Properties Ionization

10 Part 1 - Amino Acids Structure and Chemistry Building Blocks of Proteins Essential Amino Acids Basic Structure Stereochemistry Side Chain Chemistry Properties Ionization Bonding

11 Amino Acids & Proteins

12 Amino Acids & Proteins Workhorses of cell

13 Amino Acids & Proteins Workhorses of cell Catalysis

14 Amino Acids & Proteins Workhorses of cell Catalysis Signaling

15 Amino Acids & Proteins Workhorses of cell Catalysis Signaling Structure

16 Amino Acids & Proteins Workhorses of cell Catalysis Signaling Structure Energy/Gradient Generation

17 Amino Acids & Proteins Workhorses of cell Catalysis Signaling Structure Energy/Gradient Generation Proteins comprised of amino acids

18 Amino Acids Essential Amino Acids

19 Basics of Structure Elements

20 Basics of Structure Elements Alpha Amino Acids

21 Alpha Carbon Basics of Structure Elements Alpha Amino Acids

22 Alpha Carbon Basics of Structure Elements Alpha Carboxyl Alpha Amino Acids

23 Alpha Carbon Basics of Structure Elements Alpha Carboxyl Alpha Amino Acids Alpha Amine

24 Alpha Carbon Basics of Structure Elements Alpha Carboxyl Alpha Amino Acids Differences in R Groups Alpha Amine

25 Alpha Carbon Basics of Structure Elements Alpha Carboxyl Alpha Amino Acids Differences in R Groups Alpha Amine Examples

26 Alpha Carbon Basics of Structure Elements Alpha Carboxyl Alpha Amino Acids Differences in R Groups Alpha Amine Examples

27 Alpha Carbon Basics of Structure Elements Alpha Carboxyl Alpha Amino Acids Differences in R Groups Alpha Amine Examples Alpha Carbon Alpha Carboxyl R Alpha Amine

28 Alpha Carbon Basics of Structure Elements Alpha Carboxyl Alpha Amino Acids Differences in R Groups Alpha Amine Examples Asymmetric Center Alpha Carbon Alpha Carboxyl R Alpha Amine

29 Alpha Carbon Basics of Structure Elements Alpha Carboxyl Alpha Amino Acids Differences in R Groups Alpha Amine Examples

30 Alpha Carbon Basics of Structure Elements Alpha Carboxyl Alpha Amino Acids Differences in R Groups Alpha Amine Examples Alpha Carbon Alpha Carboxyl R Alpha Amine

31 Alpha Carbon Basics of Structure Elements Alpha Carboxyl Alpha Amino Acids Differences in R Groups Alpha Amine Examples Asymmetric Center Alpha Carbon Alpha Carboxyl R Alpha Amine

32 Amino Acids Stereochemistry D and L Isomers

33 Amino Acids Stereochemistry D and L Isomers

34 Amino Acids Stereochemistry D and L Isomers Asymmetric Carbon

35 Amino Acids Stereochemistry D and L Isomers Asymmetric Carbon

36 Amino Acids Stereochemistry D and L Isomers Asymmetric Carbon

37 Amino Acids Stereochemistry D and L Isomers Asymmetric Carbon Almost all biological amino acids are in the L- configuration

38 Categorizing Amino Acids Non-Polar Carboxyl Amine Aromatic Hydroxyl Other Alanine Aspartic Acid Arginine Phenylalanine Serine Asparagine Glycine Glutamic Acid Histidine Tryptophan Threonine Cysteine Isoleucine Lysine Tyrosine Tyrosine Glutamine Leucine Selenocysteine Methionine Pyrrolysine Proline Valine

39 Ionizable R- groups Name Charged R- group Approximate R- group pka Aspartic Acid Glutamic Acid - COO - - COO Lysine Arginine Histidine - NH 3 + =NH 2 + =- NH Cysteine - S Tyrosine - O

40 Amino Acids Aromatic R- Groups Tryptophan Tyrosine Phenylalanine

41 Amino Acids Aromatic R- Groups Alpha Carbon Tryptophan Alpha Amine Alpha Carboxyl Tyrosine Phenylalanine

42 Amino Acids Aromatic R- Groups R Tryptophan R R Tyrosine Phenylalanine

43 Amino Acids Aromatic R- Groups R Charges at Physiological ph Tryptophan R R Tyrosine Phenylalanine

44 Amino Acids Aromatic R- Groups R Charges at Physiological ph Tryptophan R R Ionizes at high ph Tyrosine Phenylalanine

45 Amino Acids Aliphatic R- Groups H Alanine Glycine Proline Isoleucine Leucine Valine Methionine

46 Amino Acids Aliphatic R- Groups H Alanine Glycine Proline Isoleucine Leucine Valine Methionine

47 Amino Acids Aliphatic R- Groups Charges at Physiological ph

48 Amino Acids Aliphatic R- Groups Charges at Physiological ph

49 Amino Acids Aliphatic R- Groups Charges at Physiological ph

50 Amino Acids Aliphatic R- Groups Charges at Physiological ph

51 Amino Acids Aliphatic R- Groups Charges at Physiological ph

52 Amino Acids Aliphatic R- Groups Charges at Physiological ph

53 Amino Acids Aliphatic R- Groups Charges at Physiological ph

54 Amino Acids Aliphatic R- Groups Charges at Physiological ph

55 Amino Acids R- Group Carboxyls Aspartic Acid Glutamic Acid

56 Amino Acids R- Group Carboxyls Aspartic Acid Glutamic Acid

57 Amino Acids R- Group Carboxyls Aspartic Acid Glutamic Acid

58 Amino Acids R- Group Carboxyls R R Aspartic Acid Glutamic Acid

59 Amino Acids R- Group Carboxyls Charges at physiological ph R R Aspartic Acid Glutamic Acid

60 Amino Acids Hydroxyl R- Groups Serine Threonine Tyrosine

61 Amino Acids Hydroxyl R- Groups Serine Threonine Tyrosine

62 Amino Acids Hydroxyl R- Groups Serine Threonine Tyrosine

63 Amino Acids Hydroxyl R- Groups Charges at Physiological ph Serine Threonine Ionizes at high ph Tyrosine

64 Amino Acids Hydroxyl R- Groups Charges at Physiological ph Serine Threonine Ionizes at high ph Tyrosine

65 Amino Acids Sulfhydryl R- Group Cysteine

66 Amino Acids Sulfhydryl R- Group Ionizes at about ph = 8 + Cysteine

67 Amino Acids Carboxamide R- Groups Asparagine Glutamine

68 Amino Acids Carboxamide R- Groups Asparagine Glutamine

69 Amino Acids Carboxamide R- Groups Asparagine Glutamine

70 Amino Acids Carboxamide R- Groups Asparagine Glutamine

71 Amino Acids Carboxamide R- Groups Asparagine Glutamine

72 Amino Acids Ionizable Amine R- Groups Arginine Lysine Histidine

73 Amino Acids Ionizable Amine R- Groups Arginine Lysine Histidine

74 Amino Acids Ionizable Amine R- Groups Charges at Physiological ph Arginine Lysine Histidine

75 Rare Amino Acids

76 Rare Amino Acids

77 Rare Amino Acids

78 Rare Amino Acids

79 Rare Amino Acids

80 Rare Amino Acids

81 Rare Amino Acids

82 Rare Amino Acids

83 Rare Amino Acids

84 Non- Protein Amino Acids

85 Non- Protein Amino Acids Carnitine

86 Non- Protein Amino Acids Carnitine Also - Citrulline, Ornithine, others

87 Amino Acids Ionization

88 Amino Acids Ionization - by pka Values

89 Amino Acids Ionization - by pka Values

90 Amino Acids Ionization - by pka Values

91 Amino Acids Ion Locations in Titration Charge = - 1

92 Amino Acids Ionization - by pka Values Charge = 0

93 Amino Acids Ionization - by pka Values Charge = - 1

94 Amino Acids Ionization - by pka Values Charge = - 2

95 Ionization Changes Charges Within Proteins

96 Ionization Changes Charges Within Proteins Changes in Charge Change Activities

97 Ionization Changes Charges Within Proteins Changes in Charge Change Activities

98 Post- translational Modifications

99 Post- translational Modifications

100 Post- translational Modifications

101 Post- translational Modifications

102 Post- translational Modifications

103 Phosphorylated Amino Acids

104 Phosphorylated Amino Acids

105 Phosphorylated Amino Acids

106 Phosphorylated Amino Acids

107 Phosphorylated Amino Acids

108 Breakdown of Amino Acids

109 Breakdown of Amino Acids

110 Peptide Bond Formation

111 Peptide Bond Formation

112 Metabolic Melody

113 The Amino Alphabet Song (to the tune of "The Alphabet Song") Copyright Kevin Ahern Lysine, arginine and his Basic ones you should not miss Ala, leu, val, ile, and met Fill the aliphatic set Proline bends and cys has 's' Glycine's 'R' is the smallest Then there's trp and tyr and phe Structured aromatically Asp and glu's side chains of R Say to protons "au revoir" Glutamine, asparagine Bear carboxamide amines Threonine and tiny ser Have hydroxyl groups to share These twen-ty amino A's Can combine a zillion ways

114 Metabolic Melody

115 You re Cysteine To the tune of You re Sixteen Copyright Kevin Ahern

116 You re Cysteine To the tune of You re Sixteen Copyright Kevin Ahern You re in every protein That I ve ever seen There s no need to debate You re cysteine, a building block, and you re great You give the hair waves It s something we crave Makes the food on my plate You re cysteine, a building block, and you re great Bridge That sulfhydryl in your chain Can oxidize, but I don t complain It gives support to all peptides So proteins need to have disulfides

117 You re Cysteine To the tune of You re Sixteen Copyright Kevin Ahern You re in every protein That I ve ever seen There s no need to debate You re cysteine, a building block, and you re great You give the hair waves It s something we crave Makes the food on my plate You re cysteine, a building block, and you re great Bridge That sulfhydryl in your chain Can oxidize, but I don t complain It gives support to all peptides So proteins need to have disulfides You re an acid it seems And have an amine Please don t ever mutate You re cysteine, a building block, and you re great Bridge A U-G-U or U-G-C In secret code at the cell's decree You re in my skin and in my bone And even in my glutathione You re in every protein That I ve ever seen There s no need to debate You re cysteine, a building block, and you re great

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