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BIOCHEMISTRY -
CARBOHYDRATES
Nicole Raine S. Cabasa
BIOCHEMISTRY
• “CHEMISTRY OF THE LIVING CELL”
• The study of life at the molecular level
• Lead us to fundamental understanding of life
BIOMACROMOLECULES
• Biomacromolecules are large biological polymers, such as nucleic
acids, proteins and carbohydrates, that are made up of monomers
linked together.
• Self-assemble into cellular structures and complexes
• Recognize and interact with one another in specific ways to perform
essential cellular functions
• Interactions are weal and reversible
4 MAJOR CLASSES OF
BIOMOLECULES
• CARBOHYDRATES
- mainly used as sources of cellular energy
• LIPIDS
- also known as fats; components of cell membranes
• AMINO ACIDS
- used as building blocks for proteins
• NUCLEOTIDES
- used as building blocks for DNA and RNA precursors
CARBOHYDRATES
CARBOHYDRATES
GENERAL FORMULA: Cn(H2O)n
• FUNCTIONS OF CARBOHYDRATES:
- Energy source
- Energy storage
- Carbon source
- Structure/Protection
- Recognition/Signaling
- Can be attached to other macromolecules
CARBOHYDRATES
• CLASSES OF CARBOHYDRATES:
- Monosaccharides
- Disaccharides
- Trisaccharide
- Polysaccharides (oligosaccharides)
MONOSACCHARIDES
• Common monosaccharides contain 3 to 6 carbon atoms
• Monosaccharides are either aldehydes or ketones
• For Aldoses and Ketoses – the name is based on the location of the
carbonyl (C = O)
• Combining these terms describes the essential structure of sugars
- glyceraldehyde is an aldotriose
- glucose is an aldohexose
- fructose is a ketohexose
MONOSACCHARIDES
Simplest KETOSE is
DIHYDROXYACETONE
• Contains a KETONE
• Only monosaccharide that does
not have a chiral center
Simplest ALDOSE is
GLYCERALDEHYDE
• Contains an aldehyde
• Contains a chiral center
Isomers – same
chemical formula,
different structure
Epimers – isomers that
differ at only 1 Carbon
Enantiomers – isomers
that are mirror images
(D and L)
Anomers – isomers
that differ only at
FISCHER PROJECTIONS
RULES:
• Carbons are numbered from the top
• Most oxidized C (one with the most number
of bonds to O) goes at top
• Last carbon will always be part of a CH2OH
group (Not chiral)
• If –OH is to the RIGHT -> D-isomer
• If –OH is to the LEFT -> L-isomer
CYCLIZATION OF
MONOSACCHARIDES
• TWO CASES OF CYCLIZATION:
- HEMIACETALS: Carbonyl
reacting with hydroxyl group ->
addition product called
hemiacetal. Carbon center
bonded to one R-group, a H
atom, an –OH and an –OR.
- HEMIKETALS: Hemiketal
functional group includes a
carbon center with 2 R-groups,
an –OH and an –OR group.
Formed when C5 hydroxyl
interacts with C2 carbonyl of a
ketose.
DISACCHARIDES
• Formed between monosaccharides via a glycosidic bond
• Involves OH of anomeric carbon and any other OH
DISACCHARIDES
POLYSACCHARIDES
• Two main functions:
- Energy storage
- Structure
• STORAGE POLYSACCHARIDES:
• - STARCH – found in
chloroplasts of plant cells
- Mixture of 2 types of GLUCOSE
POLYMERS: Amylose and
Amylopectin.
POLYSACCHARIDES
• STORAGE POLYSACCHARIDES:
- GLYCOGEN – animal
carbohydrate storage
Functions:
- Used to generate ATP
during anerobic muscle contraction
- The source of glucose for
maintaining blood glucose
- Stored in liver and muscle
as granules or particles
- Branched glucose
polysaccharide
POLYSACCHARIDES
GLYCOPROTEINS – oligosaccharides can also be attached to proteins
POLYSACCHARIDES
FUNCTIONS OF OLIGOSACCHARIDES ON
PROTEINS:
• Influence structure, folding and stability
of protein
• May determine the lifetime of a protein
• Serve as markers to identify a cell type
LIPIDS
• Very important biomolecules
• Insoluble in water
• Soluble in organic solvents and other lipids
• FUNCTIONS OF LIPIDS:
- Storage molecules for energy
- Structural components of cellular membranes
- Protective molecules
- Hormones and vitamins
- Intracellular messengers
- Pigments
- Insulation
LIPIDS
• FOUR MAIN CLASSES OF LIPIDS:
1. Triacylgylcerols (TAGs) – also
known as triglycerides; storage lipids
(non-polar)
2. Phosphoacylglycerols –
membrane structural lipids (polar)
3. Sphingolipids – membrane
structural lipids (polar)
4. Non-saponifiable Lipids –
steroids, hormones, cholesterol
LIPIDS
FATTY ACIDS
• Long chain carboxylic acids
• TWO TYPES:
- Saturated: - hydrocarbon has no
double bonds
- pack close together
- less fluid
- higher melting
temperature because it takes more
energy to break interactions
- likely to be solids at
room temperature
- Unsaturated: - Hydrocarbon chain
has one or more double bonds
 Do not pack as closely
 More fluid than saturated
 Lower melting temperature than saturated
 Likely to be liquid at room temperature
LIPIDS
TRIACYLGLYCEROLS
• Are made up from 3 fatty acids ester linked to glycerol
• Each –OH on glycerol can react with a fatty acid
• Start with C1 -> C2 -> C3
• Release H2O upon formation of ester linkage
LIPIDS
FAT SUBSTITUTES
• Olestra – chemically synthesized fat (TAG) substitute
• Mixture of sugars and fatty acids
•Nor absorbed and metabolized
•Depletes the body of fat soluble vitamins and may lead o
gastrointestinal distress
LIPIDS
1. TRIACYLGLYCEROLS
- hydrolyzed into 3 fatty acids and 1 glycerolSAPONIFICATION:
LIPIDS
2. PHOSPHOACYLGLYCEROLS
- very similar in structure to triacylglycerols except one of the
alcohols of glycerol is esterified by phosphoric acid instead of fatty
acid = phosphatidic acid
- the phosphoric acid group is then esterified by a second
alcohol to form the phosphoacylglycerol
LIPIDS
3. SPHINGOLIPIDS
- membrane lipids based on the core structure of SPHINGOSINE,
a long chain amino alcohol
- Glycerol is replaced by sphingosine
LIPIDS
4. NON-SAPONIFIABLE LIPIDS/STEROIDS
- based on a fused ring system – RIGID structure
- No ester linkages
- Includes hormones
LIPIDS
BIOLOGICAL MEMBRANES
• Membranes surround all cells and organelles
• Membranes are based on LIPID BILAYERS (phospholipids,
glycosphingolipids, sphingolipids and cholesterol)
• Non-polar components minimize exposure to water by forming a
bilayer
• Polar head groups face outward and H-bond with water
• Lipid fatty acid chains face inward and interact via hydrophobic
interactions
LIPIDS
EFFECT OF CHOLESTEROL ON MEMBRANES
• Bulky rigid molecule
• Moderates fluidity of membranes
- Cholesterol in membranes decreases fluidity because it is
rigid
- Prevents crystallization (making solid) of fatty acyl side chains
by fitting between them. Disrupts close packing of fatty acyl chains.
Thus, increased fluidity.
LIPIDS
INTEGRAL MEMBRANE PROTEINS
• Located within the lipid bilayer
• Hydrophobic amino acids interact with fatty acid chains in the hydrophobic
core of the membrane
•Usually span the bilayer one or more times – called transmembrane proteins
• FUNCTIONS: Transporters & Receptors
• Beta-Barrel Integral Membrane Proteins – barrel shaped protein that is made
up of antiparallel beta strands with hydrophilic head and hydrophobic tails
• Alpha-Helical Membrane Proteins – can cross the membrane once or many
times and have multiple transmembrane segments. Major category of
transmembrane proteins.
LIPIDS
PERPHERAL MEMBRANE PROTEINS
• Interact weakly with the membrane with lipid head groups or integral
membrane proteins
• Interactions are mainly hydrogen bonds or electrostatic interactions
• Functions: enzymes, signal transduction proteins, cytoskeletal
proteins
• Lipid anchors protein in the membrane: Farnesyl, Myristoyl, Palmitoyl
LIPIDS
FLUID MOSAIC MODEL OF MEMBRANE STRUCTURE
LIPIDS
MEMBRANE FUNCTION
- Separate cytoplasm from environment
- Provide system for uptake and export of compounds
- Mediate interactions with environment
- Provide environment for catalysis
MEMBRANE TRANSPORT
CLASSES OF ACTIVE AND PASSIVE TRANSPORTERS
• Symporters – moves a small molecule inside a cell during transport
of target molecule inside a cell
• Antiporters – moves a small molecule outside the cell during
transport of a target molecule inside a cell
• Uniporters – binds and transports target molecule only
MEMBRANE TRANSPORT
PASSIVE TRANSPORT
- move from HIGHER concentration to LOWER concentration
region
- no need for energy input for this transport
- Two types:
Simple Diffusion – molecule passes through membrane
pore opening without interacting with other molecules
Facilitated Diffusion – transport assisted by specific
membrane protein
MEMBRANE TRANSPORT
ACTIVE TRANSPORT
- move from LOW concentration
area to HIGH concentration area
- cells must use energy to
transport. ATP is used.
- Examples: Glucose Transport into
Intestinal Cells
Na+-K+ Ion Pump
THANK YOU!

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Carbohydrates

  • 2. BIOCHEMISTRY • “CHEMISTRY OF THE LIVING CELL” • The study of life at the molecular level • Lead us to fundamental understanding of life
  • 3.
  • 4. BIOMACROMOLECULES • Biomacromolecules are large biological polymers, such as nucleic acids, proteins and carbohydrates, that are made up of monomers linked together. • Self-assemble into cellular structures and complexes • Recognize and interact with one another in specific ways to perform essential cellular functions • Interactions are weal and reversible
  • 5. 4 MAJOR CLASSES OF BIOMOLECULES • CARBOHYDRATES - mainly used as sources of cellular energy • LIPIDS - also known as fats; components of cell membranes • AMINO ACIDS - used as building blocks for proteins • NUCLEOTIDES - used as building blocks for DNA and RNA precursors
  • 7. CARBOHYDRATES GENERAL FORMULA: Cn(H2O)n • FUNCTIONS OF CARBOHYDRATES: - Energy source - Energy storage - Carbon source - Structure/Protection - Recognition/Signaling - Can be attached to other macromolecules
  • 8. CARBOHYDRATES • CLASSES OF CARBOHYDRATES: - Monosaccharides - Disaccharides - Trisaccharide - Polysaccharides (oligosaccharides)
  • 9. MONOSACCHARIDES • Common monosaccharides contain 3 to 6 carbon atoms • Monosaccharides are either aldehydes or ketones • For Aldoses and Ketoses – the name is based on the location of the carbonyl (C = O) • Combining these terms describes the essential structure of sugars - glyceraldehyde is an aldotriose - glucose is an aldohexose - fructose is a ketohexose
  • 10. MONOSACCHARIDES Simplest KETOSE is DIHYDROXYACETONE • Contains a KETONE • Only monosaccharide that does not have a chiral center Simplest ALDOSE is GLYCERALDEHYDE • Contains an aldehyde • Contains a chiral center Isomers – same chemical formula, different structure Epimers – isomers that differ at only 1 Carbon Enantiomers – isomers that are mirror images (D and L) Anomers – isomers that differ only at
  • 11. FISCHER PROJECTIONS RULES: • Carbons are numbered from the top • Most oxidized C (one with the most number of bonds to O) goes at top • Last carbon will always be part of a CH2OH group (Not chiral) • If –OH is to the RIGHT -> D-isomer • If –OH is to the LEFT -> L-isomer
  • 12. CYCLIZATION OF MONOSACCHARIDES • TWO CASES OF CYCLIZATION: - HEMIACETALS: Carbonyl reacting with hydroxyl group -> addition product called hemiacetal. Carbon center bonded to one R-group, a H atom, an –OH and an –OR. - HEMIKETALS: Hemiketal functional group includes a carbon center with 2 R-groups, an –OH and an –OR group. Formed when C5 hydroxyl interacts with C2 carbonyl of a ketose.
  • 13. DISACCHARIDES • Formed between monosaccharides via a glycosidic bond • Involves OH of anomeric carbon and any other OH
  • 15. POLYSACCHARIDES • Two main functions: - Energy storage - Structure • STORAGE POLYSACCHARIDES: • - STARCH – found in chloroplasts of plant cells - Mixture of 2 types of GLUCOSE POLYMERS: Amylose and Amylopectin.
  • 16. POLYSACCHARIDES • STORAGE POLYSACCHARIDES: - GLYCOGEN – animal carbohydrate storage Functions: - Used to generate ATP during anerobic muscle contraction - The source of glucose for maintaining blood glucose - Stored in liver and muscle as granules or particles - Branched glucose polysaccharide
  • 17. POLYSACCHARIDES GLYCOPROTEINS – oligosaccharides can also be attached to proteins
  • 18. POLYSACCHARIDES FUNCTIONS OF OLIGOSACCHARIDES ON PROTEINS: • Influence structure, folding and stability of protein • May determine the lifetime of a protein • Serve as markers to identify a cell type
  • 19. LIPIDS • Very important biomolecules • Insoluble in water • Soluble in organic solvents and other lipids • FUNCTIONS OF LIPIDS: - Storage molecules for energy - Structural components of cellular membranes - Protective molecules - Hormones and vitamins - Intracellular messengers - Pigments - Insulation
  • 20. LIPIDS • FOUR MAIN CLASSES OF LIPIDS: 1. Triacylgylcerols (TAGs) – also known as triglycerides; storage lipids (non-polar) 2. Phosphoacylglycerols – membrane structural lipids (polar) 3. Sphingolipids – membrane structural lipids (polar) 4. Non-saponifiable Lipids – steroids, hormones, cholesterol
  • 21. LIPIDS FATTY ACIDS • Long chain carboxylic acids • TWO TYPES: - Saturated: - hydrocarbon has no double bonds - pack close together - less fluid - higher melting temperature because it takes more energy to break interactions - likely to be solids at room temperature - Unsaturated: - Hydrocarbon chain has one or more double bonds  Do not pack as closely  More fluid than saturated  Lower melting temperature than saturated  Likely to be liquid at room temperature
  • 22. LIPIDS TRIACYLGLYCEROLS • Are made up from 3 fatty acids ester linked to glycerol • Each –OH on glycerol can react with a fatty acid • Start with C1 -> C2 -> C3 • Release H2O upon formation of ester linkage
  • 23. LIPIDS FAT SUBSTITUTES • Olestra – chemically synthesized fat (TAG) substitute • Mixture of sugars and fatty acids •Nor absorbed and metabolized •Depletes the body of fat soluble vitamins and may lead o gastrointestinal distress
  • 24. LIPIDS 1. TRIACYLGLYCEROLS - hydrolyzed into 3 fatty acids and 1 glycerolSAPONIFICATION:
  • 25. LIPIDS 2. PHOSPHOACYLGLYCEROLS - very similar in structure to triacylglycerols except one of the alcohols of glycerol is esterified by phosphoric acid instead of fatty acid = phosphatidic acid - the phosphoric acid group is then esterified by a second alcohol to form the phosphoacylglycerol
  • 26. LIPIDS 3. SPHINGOLIPIDS - membrane lipids based on the core structure of SPHINGOSINE, a long chain amino alcohol - Glycerol is replaced by sphingosine
  • 27. LIPIDS 4. NON-SAPONIFIABLE LIPIDS/STEROIDS - based on a fused ring system – RIGID structure - No ester linkages - Includes hormones
  • 28. LIPIDS BIOLOGICAL MEMBRANES • Membranes surround all cells and organelles • Membranes are based on LIPID BILAYERS (phospholipids, glycosphingolipids, sphingolipids and cholesterol) • Non-polar components minimize exposure to water by forming a bilayer • Polar head groups face outward and H-bond with water • Lipid fatty acid chains face inward and interact via hydrophobic interactions
  • 29. LIPIDS EFFECT OF CHOLESTEROL ON MEMBRANES • Bulky rigid molecule • Moderates fluidity of membranes - Cholesterol in membranes decreases fluidity because it is rigid - Prevents crystallization (making solid) of fatty acyl side chains by fitting between them. Disrupts close packing of fatty acyl chains. Thus, increased fluidity.
  • 30. LIPIDS INTEGRAL MEMBRANE PROTEINS • Located within the lipid bilayer • Hydrophobic amino acids interact with fatty acid chains in the hydrophobic core of the membrane •Usually span the bilayer one or more times – called transmembrane proteins • FUNCTIONS: Transporters & Receptors • Beta-Barrel Integral Membrane Proteins – barrel shaped protein that is made up of antiparallel beta strands with hydrophilic head and hydrophobic tails • Alpha-Helical Membrane Proteins – can cross the membrane once or many times and have multiple transmembrane segments. Major category of transmembrane proteins.
  • 31. LIPIDS PERPHERAL MEMBRANE PROTEINS • Interact weakly with the membrane with lipid head groups or integral membrane proteins • Interactions are mainly hydrogen bonds or electrostatic interactions • Functions: enzymes, signal transduction proteins, cytoskeletal proteins • Lipid anchors protein in the membrane: Farnesyl, Myristoyl, Palmitoyl
  • 32. LIPIDS FLUID MOSAIC MODEL OF MEMBRANE STRUCTURE
  • 33. LIPIDS MEMBRANE FUNCTION - Separate cytoplasm from environment - Provide system for uptake and export of compounds - Mediate interactions with environment - Provide environment for catalysis
  • 34. MEMBRANE TRANSPORT CLASSES OF ACTIVE AND PASSIVE TRANSPORTERS • Symporters – moves a small molecule inside a cell during transport of target molecule inside a cell • Antiporters – moves a small molecule outside the cell during transport of a target molecule inside a cell • Uniporters – binds and transports target molecule only
  • 35. MEMBRANE TRANSPORT PASSIVE TRANSPORT - move from HIGHER concentration to LOWER concentration region - no need for energy input for this transport - Two types: Simple Diffusion – molecule passes through membrane pore opening without interacting with other molecules Facilitated Diffusion – transport assisted by specific membrane protein
  • 36. MEMBRANE TRANSPORT ACTIVE TRANSPORT - move from LOW concentration area to HIGH concentration area - cells must use energy to transport. ATP is used. - Examples: Glucose Transport into Intestinal Cells Na+-K+ Ion Pump