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Chemistry of Carbon

             Building Blocks of Life




AP Biology                             2007-2008
Why study Carbon?
      All of life is built on carbon
      Cells
            ~72% H2O
            ~25% carbon compounds
              carbohydrates
              lipids
              proteins
              nucleic acids
            ~3% salts
AP Biology    Na, Cl, K…
Chemistry of Life
     Organic chemistry is the study of
       carbon compounds
      C atoms are versatile building blocks
          bonding properties
          4 stable covalent bonds



                           H

                           C
                       H        H
                           H
AP Biology
Complex molecules assembled like TinkerToys




AP Biology
Hydrocarbons
      Combinations of C & H
            non-polar
              not soluble in H2O
              hydrophobic                  methane
                                           (simplest HC)
          stable
          very little attraction

           between molecules
              a gas at room temperature

AP Biology
Hydrocarbons can grow




AP Biology
Isomers
     Molecules with same molecular formula
        but different structures (shapes)
          different chemical properties
          different biological functions




             6 carbons
                                        6 carbons


AP Biology               6 carbons
Form affects function
     Structural differences create important
        functional significance
            amino acid alanine
              L-alanine used in proteins
              but not D-alanine
            medicines
              L-version active
              but not D-version
            sometimes with
             tragic results…
AP Biology
                         stereoisomers
Form affects function
    Thalidomide
         prescribed to pregnant women in 50s & 60s
         reduced morning sickness, but…

         stereoisomer caused severe birth defects




AP Biology
Diversity of molecules
    Substitute other atoms or groups
        around the carbon
            ethane vs. ethanol
              H replaced by an hydroxyl group (–OH)
              nonpolar vs. polar
              gas vs. liquid
              biological effects!




AP Biology   ethane (C2H6)             ethanol (C2H5OH)
Functional groups
     Parts of organic molecules that are
        involved in chemical reactions
            give organic molecules distinctive
             properties
               hydroxyl        amino
               carbonyl        sulfhydryl
               carboxyl        phosphate
      Affect reactivity
          makes hydrocarbons hydrophilic
          increase solubility in water


AP Biology
Viva la difference!
      Basic structure of male & female
        hormones is identical
            identical carbon skeleton
            attachment of different functional groups
            interact with different targets in the body
               different effects




AP Biology
Hydroxyl
     –OH
          organic compounds with OH = alcohols
          names typically end in -ol

              ethanol




AP Biology
Carbonyl
     C=O
            O double bonded to C
              if C=O at end molecule = aldehyde
              if C=O in middle of molecule = ketone




AP Biology
Carboxyl
     –COOH
            C double bonded to O & single bonded
             to OH group
              compounds with COOH = acids
                 fatty acids
                 amino acids




AP Biology
Amino
     -NH2
            N attached to 2 H
               compounds with NH2 = amines
                  amino acids
               NH2 acts as base
                 ammonia picks up H+ from solution




AP Biology
Sulfhydryl
     –SH
            S bonded to H
              compounds with SH = thiols
              SH groups stabilize the structure of proteins




AP Biology
Phosphate
    –PO4
            P bound to 4 O
              connects to C through an O
              lots of O = lots of negative charge
                  highly reactive
              transfers energy between organic molecules
                  ATP, GTP, etc.




AP Biology
Macromolecules

      Building Blocks
           of Life




AP Biology              2007-2008
Macromolecules
     Smaller organic molecules join together
        to form larger molecules
            macromolecules
      4 major classes of
        macromolecules:
          carbohydrates
          lipids

          proteins

          nucleic acids



AP Biology
Polymers
    Long molecules built by linking repeating
       building blocks in a chain
            monomers
              building blocks
              repeated small units
                                                   H2O
            covalent bonds
                          HO          H   HO       H


 Dehydration synthesis

                               HO              H
AP Biology
How to build a polymer                  You gotta
                                           be open to
                                           “bonding!
     Synthesis
            joins monomers by “taking” H2O out
              one monomer donates OH–
              other monomer donates H+
              together these form H2O
                                                            H2O
            requires energy & enzymes
                        HO                 H   HO           H
                                          enzyme
Dehydration synthesis
Condensation reaction
                             HO                         H
AP Biology
How to break down a polymer
                                                     Breaking up
      Digestion                                   is hard to do!

            use H2O to breakdown polymers
              reverse of dehydration synthesis
              cleave off one monomer at a time
              H2O is split into H+ and OH–
                                                                    H2O
                 H+ & OH– attach to ends
          requires enzymes
                           HO                                H
          releases energy                    enzyme
            Hydrolysis

AP Biology
             Digestion         HO              H     HO             H
Any Questions??




AP Biology           2007-2008

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Macromolecule overview

  • 1. Chemistry of Carbon Building Blocks of Life AP Biology 2007-2008
  • 2. Why study Carbon?  All of life is built on carbon  Cells  ~72% H2O  ~25% carbon compounds  carbohydrates  lipids  proteins  nucleic acids  ~3% salts AP Biology  Na, Cl, K…
  • 3. Chemistry of Life  Organic chemistry is the study of carbon compounds  C atoms are versatile building blocks  bonding properties  4 stable covalent bonds H C H H H AP Biology
  • 4. Complex molecules assembled like TinkerToys AP Biology
  • 5. Hydrocarbons  Combinations of C & H  non-polar  not soluble in H2O  hydrophobic methane (simplest HC)  stable  very little attraction between molecules  a gas at room temperature AP Biology
  • 7. Isomers  Molecules with same molecular formula but different structures (shapes)  different chemical properties  different biological functions 6 carbons 6 carbons AP Biology 6 carbons
  • 8. Form affects function  Structural differences create important functional significance  amino acid alanine  L-alanine used in proteins  but not D-alanine  medicines  L-version active  but not D-version  sometimes with tragic results… AP Biology stereoisomers
  • 9. Form affects function  Thalidomide  prescribed to pregnant women in 50s & 60s  reduced morning sickness, but…  stereoisomer caused severe birth defects AP Biology
  • 10. Diversity of molecules  Substitute other atoms or groups around the carbon  ethane vs. ethanol  H replaced by an hydroxyl group (–OH)  nonpolar vs. polar  gas vs. liquid  biological effects! AP Biology ethane (C2H6) ethanol (C2H5OH)
  • 11. Functional groups  Parts of organic molecules that are involved in chemical reactions  give organic molecules distinctive properties hydroxyl amino carbonyl sulfhydryl carboxyl phosphate  Affect reactivity  makes hydrocarbons hydrophilic  increase solubility in water AP Biology
  • 12. Viva la difference!  Basic structure of male & female hormones is identical  identical carbon skeleton  attachment of different functional groups  interact with different targets in the body  different effects AP Biology
  • 13. Hydroxyl  –OH  organic compounds with OH = alcohols  names typically end in -ol  ethanol AP Biology
  • 14. Carbonyl  C=O  O double bonded to C  if C=O at end molecule = aldehyde  if C=O in middle of molecule = ketone AP Biology
  • 15. Carboxyl  –COOH  C double bonded to O & single bonded to OH group  compounds with COOH = acids  fatty acids  amino acids AP Biology
  • 16. Amino  -NH2  N attached to 2 H  compounds with NH2 = amines  amino acids  NH2 acts as base  ammonia picks up H+ from solution AP Biology
  • 17. Sulfhydryl  –SH  S bonded to H  compounds with SH = thiols  SH groups stabilize the structure of proteins AP Biology
  • 18. Phosphate  –PO4  P bound to 4 O  connects to C through an O  lots of O = lots of negative charge  highly reactive  transfers energy between organic molecules  ATP, GTP, etc. AP Biology
  • 19. Macromolecules Building Blocks of Life AP Biology 2007-2008
  • 20. Macromolecules  Smaller organic molecules join together to form larger molecules  macromolecules  4 major classes of macromolecules:  carbohydrates  lipids  proteins  nucleic acids AP Biology
  • 21. Polymers  Long molecules built by linking repeating building blocks in a chain  monomers  building blocks  repeated small units H2O  covalent bonds HO H HO H Dehydration synthesis HO H AP Biology
  • 22. How to build a polymer You gotta be open to “bonding!  Synthesis  joins monomers by “taking” H2O out  one monomer donates OH–  other monomer donates H+  together these form H2O H2O  requires energy & enzymes HO H HO H enzyme Dehydration synthesis Condensation reaction HO H AP Biology
  • 23. How to break down a polymer Breaking up  Digestion is hard to do!  use H2O to breakdown polymers  reverse of dehydration synthesis  cleave off one monomer at a time  H2O is split into H+ and OH– H2O  H+ & OH– attach to ends  requires enzymes HO H  releases energy enzyme Hydrolysis AP Biology Digestion HO H HO H

Editor's Notes

  1. Why do we study carbon -- is it the most abundant element in living organisms? H & O most abundant C is the next most abundant
  2. Carbon chemistry = organic chemistry Why is it a foundational atom? What makes it so important? Can’t be a good building block if you only form 1 or 2 bonds.
  3. Like sugars: C 6 H 12 O 6 But can be arranged in different ways -glucose -galactose -dextrose
  4. Same formula but different structurally & therefore different functionally. Molecular shape determines biological properties. Ex. Isomers may be ineffective as medicines
  5. For example the male and female hormones, testosterone and estradiol, differ from each other only by the attachment of different functional groups to an identical carbon skeleton.
  6. • great variety of polymers can be built from a small set of monomers • monomers can be connected in many combinations like the 26 letters in the alphabet can be used to create a great diversity of words • each cell has millions of different macromolecules
  7. Most macromolecules are polymers • build: condensation (dehydration) reaction • breakdown: hydrolysis An immense variety of polymers can be built from a small set of monomers