Chapter 2, Part 2: The Chemistry of Life
Todays TopicsOrganic MoleculesCarbon & Biological
SystemsMonomers & PolymersSugars/CarbohydratesFatty
Acids/LipidsAmino Acids/ProteinsNucleic Acids/DNA & RNAWhen
Things Go SouthChemistry of Life, Part 2
Part 2Chapter 2
BIO156Paradise Valley Community College#
13/5/2017Paradise Valley Community CollegeThe Chemistry of Life,
Part 2
Modeling an Organic Molecule
CyclohexaneBenzeneMethaneCCCCCCHHHHHHHHHHHH
Source: http://www.google.com/. 2013.
BIO156Paradise Valley Community College#2
The Chemistry of Life, Part 2Paradise Valley Community
College3/5/2017
Building Organic MoleculesCarbon atoms bond with up to four
other atoms...
methanemethanolethaneethanol
BIO156Paradise Valley Community College#3
The Chemistry of Life, Part 2Paradise Valley Community
College3/5/2017
Carbon atoms bond with up to four other atomsoften forming long
chains or rings. Building Organic Molecules
MethaneCH4
Linoleic acid (cis isomer)Linolelaidic acid (trans isomer)
Source: Starr, C., Evers, C. A., & Starr, L. 2014.
C18H32O2
BIO156Paradise Valley Community College#4
The Chemistry of Life, Part 2Paradise Valley Community
College3/5/2017
Anabolism:Enzymes also create polymers from component
monomers.Metabolism
Catabolism:Enzymes break apart polymers into component
monomers.
biopolymer
enzymeMetabolism:A complex of physical and chemical
processeswithin a living cell or organism, necessary for the
maintenance of life
BIO156Paradise Valley Community College#5
The Chemistry of Life, Part 2Paradise Valley Community
College3/5/2017
simple sugarsfatty acidsamino acidsnucleotidesMonomersubunit of
a polymersimple sugarsfatty acidsamino
acidsnucleotidesPolymerconsists of multiple
monomerscarbohydrateslipidsproteinsnucleic acids
Monomers and Polymers GlucoseSucroseFructose
HCCCCCCHHHHHOOOOOOHHHHHHHCCCCCCHHHHHOOOOOHHHHHOH............
BIO156Paradise Valley Community College#6
The Chemistry of Life, Part 2Paradise Valley Community
College3/5/2017
GlucoseGlucose, Fructose, and GalactoseSix-carbon sugars
(hexoses)Dietary monosaccharidesC6H12O6 Ribose and
DeoxyriboseFive-carbon sugars (pentoses)Backbone sugars for RNA and
DNAC5H10O5
6 Oxygens12 Hydrogens6 CarbonsLets count them
Glucose
Five Common Sugars
FructoseGalactose
Ribose
Deoxyribose
BIO156Paradise Valley Community College#
BIO156Paradise Valley Community College#7
The Chemistry of Life, Part 2Paradise Valley Community
College3/5/2017
Common Sugars
NutraSweet(aspartame)
Splenda(sucralose)
Stevia(steviol)200-600 timessweeter thansucrose
SucroseSource: commons.wikimedia.org. 2015
BIO156Paradise Valley Community College#8
The Chemistry of Life, Part 2Paradise Valley Community
College3/5/2017
OHOHDehydration Reaction
GlucoseGlucose
Water removedenzymaticallyMaltose
Dehydration
BIO156Paradise Valley Community College#9
The Chemistry of Life, Part 2Paradise Valley Community
College3/5/2017
Hydrolysis
ReactionGlucoseSucroseFructosePolysaccharide(Disaccharide)(Monosaccharides)
HOH
H
Bond splitenzymaticallyby adding waterHydrolysis
BIO156Paradise Valley Community College#10
The Chemistry of Life, Part 2Paradise Valley Community
College3/5/2017
Sugars Why We Love Them
BIO156Paradise Valley Community College#Cells use carbohydrates
for energy and structural materials.
CarbohydratesCarbohydratesMolecules that consist primarily of
carbon, hydrogen, and oxygen
atomsGlucoseC6H12O6SucroseC12H22O11Amylose(C6H10O5)n
Credit: gymflow100.com. 2015.
BIO156Paradise Valley Community College#12
The Chemistry of Life, Part 2Paradise Valley Community
College3/5/2017
Complex CarbohydratesEnzymes assemble complex carbohydrates
(polysaccharides) from simple carbohydrate (monosaccharide)
subunits.Glucose monomers can bond in different patterns to form
different complex carbohydrates.Starch (main energy reserve in
plants)Cellulose (structural component of plants)Glycogen (energy
reserve in animals)
Source: bakerpedia.com. 2015.
Source: galleryhip.com. 2015.
Source: www.livestrong.com. 2015.
BIO156Paradise Valley Community College#13
The Chemistry of Life, Part 2Paradise Valley Community
College3/5/2017
Complex Carbohydrates: Starch
Source: Modified from courses.bio.indiana.edu. 2013.
BIO156Paradise Valley Community College#14
The Chemistry of Life, Part 2Paradise Valley Community
College3/5/2017
Complex Carbohydrates: CelluloseFound only in plants.H-Bonding
createsstraight chains.
Source: modified from cegep-ste-foy.qc.ca. 2015.
Source: Modified from courses.bio.indiana.edu. 2013.
BIO156Paradise Valley Community College#15
The Chemistry of Life, Part 2Paradise Valley Community
College3/5/2017
Complex Carbohydrates: Glycogen
Branched-chainCarbohydrateCross-section of glycogengranule with
protein in center
Source: Modified from courses.bio.indiana.edu2013.
10-40 m10-40 x 10-6 mDiam. Human Hair100 x 10-6mGlycogen
granuleSource: commons.wikimedia.org. 2015.
BIO156Paradise Valley Community College#Todays TopicsOrganic
MoleculesCarbon, Metabolism, and Biological SystemsMonomers &
PolymersSugars/CarbohydratesFatty Acids/LipidsAmino
Acids/ProteinsNucleic Acids/DNA & RNAWhen Things Go
SouthChemistry of Life, Part 2
BIO156Paradise Valley Community College#
173/5/2017Paradise Valley Community CollegeThe Chemistry of
Life, Part 2
LipidsLipids are greasy or oily nonpolar organic molecules,
often with one or more fatty acid tails.Lipid:oily or waxy
compoundscomposed of:long chain of carbon atoms (fatty
acids)hydrophobicwith an acidic carboxyl group at one
endhydrophilicSource: Modified from Koeppen & Stanton.
2015.Steroid
Glycolipid
Phospholipid
BIO156Paradise Valley Community College#18
The Chemistry of Life, Part 2Paradise Valley Community
College3/5/2017
TriglyceridesFatty AcidsGlycerolTriglyceride
BIO156Paradise Valley Community College#Fats (e.g.,
triglycerides, lipids) most abundant source of energy in
vertebratesstored in adipose tissue that insulates the
bodyFat:Lipid with one, two, orthree fatty acid
tailsTriglyceride:Lipid with three fattyacid tails attachedto a
glycerol backboneFats
Source: modified from ww.medicinenet.com. 2015.Credit: Sanju
Varghese. slideshare.net. 2015.
Source: dani-fabulous.com. 2015.adipose tissue
BIO156Paradise Valley Community College#
BIO156Paradise Valley Community College#20
The Chemistry of Life, Part 2Paradise Valley Community
College3/5/2017
WaxesWaxes are a category of water-repellent and lubricating
secretions in plants and animals.Wax (Cerumen)Water-repellent lipid
with long fatty-acid tails bonded to long-chain alcohols or carbon
rings
Source: Modified from bessergesundleben.com. 2015.
BIO156Paradise Valley Community College#
BIO156Paradise Valley Community College#21
The Chemistry of Life, Part 2Paradise Valley Community
College3/5/2017
Saturated and Unsaturated FatsSaturated fats pack more tightly
than unsaturated fats, and tend to be more solid.Saturated
fat:Fatty acid with no doublebonds in its carbon tailUnsaturated
fat:Lipid with one or moredouble bonds in a fattyacid tail
Source: Modified from online.science.psu.edu. 2015.Saturated
fats
Source: Modified from online.science.psu.edu. 2015.Unsaturated
fats
Source: www.cobrinhabjj.com. 2015
mono-unsaturated
poly-unsaturated
saturated
BIO156Paradise Valley Community College#22
The Chemistry of Life, Part 2Paradise Valley Community
College3/5/2017
Fatty AcidsStearicacidLinolenicacidOleicacidElaidicacidCarboxyl
group17-Carbon chainsPolarRegionNonpolarRegion
Cocoa ButterCanolaOilOliveOilTransFat
LiquidSolidSolidLiquid
BIO156Paradise Valley Community College#Omega Fatty AcidsSource:
iherb.com/DHA. 2017.
Source: en.Wikipedia..com. 2016.
Source: Modified from eufic.org. 2016.
OmegaEndOmega-3FattyAcidsOmegaEndOmega-6FattyAcids
BIO156Paradise Valley Community College#Source: Modified
hammiverse.com 2017.
PhospholipidsPhospholipids are the main structural component of
cell membranes.Phospholipid:A lipid with a phosphate group in its
hydrophilic head, andtwo nonpolar fatty acid tails
The Dancing Baker
BIO156Paradise Valley Community College#
BIO156Paradise Valley Community College#25
The Chemistry of Life, Part 2Paradise Valley Community
College3/5/2017
Source: teebioscience.blogspot.com. 2015.
Lipid BilayerOne layer of phospholipidsOne layer of
phospholipidsThe Fluid Mosaic Model of the Cell Membrane
BIO156Paradise Valley Community College#26Figure
2.15Phospholipids. (A) Each phospholipid has a hydrophilic head and
two hydrophobic tails. (B) A double layer of phospholipids is the
structural foundation of all cell membranes.The Chemistry of Life,
Part 2Paradise Valley Community College3/5/2017
Source: en.wikipedia.com. 2015.SteroidsSteroids such as
cholesterol occur in cell membranes or are remodeled into other
molecules (such as steroidal hormones, bile salts, and vitamin
D).Steroid:17 Carbon atoms but in a ringstructure with a carbon
tailA type of lipid with fourcarbon rings and nofatty acid
tails
Source: en.wikipedia.com. 2015.
1234
BIO156Paradise Valley Community College#
BIO156Paradise Valley Community College#27
The Chemistry of Life, Part 2Paradise Valley Community
College3/5/2017
Cholesterol & Steroidal HormonesEstrogenTestosterone
To make this happen, one needs
enzymes.ProgesteroneCholesterol
BIO156Paradise Valley Community College#ProteinsThe function of
a protein depends on its structure, which consists of chains of
amino acids that twist and fold into functional
domains.Protein:Organic compoundthat consists of achain or chains
ofamino acids
Source: www.dailyhealthtips24.com. 2015.
BIO156Paradise Valley Community College#29
The Chemistry of Life, Part 2Paradise Valley Community
College3/5/2017
Amino AcidsAmino acidSmall organic compound with a carboxyl
group,amino group, and a characteristic side group (R).
Amino groupCarboxyl group
BIO156Paradise Valley Community College#30
The Chemistry of Life, Part 2Paradise Valley Community
College3/5/2017
Definitions: Peptide BondsAmino acids are joined by chains of
peptide bonds into a structure called a polypeptide.Peptide
bond:Bond between the amino group of one amino acid and the
carboxyl group of anotherPolypeptide:Chain of amino acids linked by
peptide bonds
BIO156Paradise Valley Community College#31
The Chemistry of Life, Part 2Paradise Valley Community
College3/5/2017
20 Naturally Occurring Amino Acids
NucleophilicHydrophilicAromaticAcidicAmideBasicSmallSource:
Modified from nptel.ac.in. 2017.
PhenylalanineValineTryptophanTyrosineIsoleucineMethionineHistidinealanineLeucineLysineEssentialAmino
Acids
BIO156Paradise Valley Community College#Source: Modified from
study.com. 2014.
Peptide FormationDipeptideWaterAmino Acid 1Amino Acid 2
R represents the side chain which defines the amino acid.
Peptide Bond
BIO156Paradise Valley Community College#33
The Chemistry of Life, Part 2Paradise Valley Community
College3/5/2017
Protein structure1. Primary structure (polypeptide formation)
Simply, a linear sequence of amino acids
BIO156Paradise Valley Community College#
BIO156Paradise Valley Community College#34
The Chemistry of Life, Part 2Paradise Valley Community
College3/5/2017
Source: www.biomoleculeobjects.com. 2015.Protein structure2.
Secondary structureHydrogen bonds twist the polypeptide into a coil
or sheet.-helix-sheets -helix
Credit: modified from commons.wikimedia.org.
2015.-helix-sheets
BIO156Paradise Valley Community College#
BIO156Paradise Valley Community College#35
The Chemistry of Life, Part 2Paradise Valley Community
College3/5/2017
Protein structure3. Tertiary structureSecondary structure folds
into a functional shape.
Source: www.biomoleculeobjects.com. 2015.
Heme
Hemoglobin
BIO156Paradise Valley Community College#
BIO156Paradise Valley Community College#36
The Chemistry of Life, Part 2Paradise Valley Community
College3/5/2017
Protein structure4. Quaternary structure (Optional) Two or more
distinct polypeptide chains associate and function as one molecule
(e.g., hemoglobin).
Credit: Modified from Lietuvos Sveikatos. Slideshar.net.
2015
BIO156Paradise Valley Community College#
BIO156Paradise Valley Community College#37
The Chemistry of Life, Part 2Paradise Valley Community
College3/5/2017
1. Primary structure (polypeptide formation) Simply, a linear
sequence of amino acids2. Secondary structureHydrogen bonds twist
the polypeptide into a coil or sheet.3. Tertiary structureSecondary
structure folds into a functional shape.4. Quaternary structure
(Optional) Two or more distinct polypeptide chains associate and
function as one molecule.Protein Structure A Review
BIO156Paradise Valley Community College#38
The Chemistry of Life, Part 2Paradise Valley Community
College3/5/2017
What is a Protein?
BIO156Paradise Valley Community College#
Source: modified from SofiaPazM. Slideshare.net. 2015.Protein
irreversibly denaturesImportance of Protein StructureChanges in a
proteins structure at any level may also alter its function.
Albumenwater-solubleinsolubleDenaturing Albumin
Source: Modified from mpibpc.mpg.de. 2017.irreversible
denaturation
BIO156Paradise Valley Community College#
BIO156Paradise Valley Community College#40
The Chemistry of Life, Part 2Paradise Valley Community
College3/5/2017
HOH
HOH
Nucleotide:Monomer of nucleic acidsHas a five-carbon sugar,a
nitrogen-containing base,and phosphate groups
NucleosideNucleic AcidsRiboseNitrogenousBase
HOHHOH
Nucleotide diphosphateNucleotide monophosphateNucleotide
triphosphate
High energy bonds
BIO156Paradise Valley Community College#41
The Chemistry of Life, Part 2Paradise Valley Community
College3/5/2017
ATPThe nucleotide, ATP, cantransfer energy to other
molecules,andis important in metabolism.Adenosine triphosphate
(ATP)Nucleotide that consists of anadenine base,five-carbon ribose
sugar,and three phosphate groupsFunctions as an energy carrier
Source: commons.wikimedia.org. 2015.
BIO156Paradise Valley Community College#
BIO156Paradise Valley Community College#42
The Chemistry of Life, Part 2Paradise Valley Community
College3/5/2017
Nucleic AcidsNucleic acidsNucleotide monomers joined by
sugar-phosphate bonds
DNARNAC
O- O P O CH2OG
O- O P O CH2OTO- O P O CH2O
A
O- O P O CH2OA
O- O P O CH2OU
O- O P O CH2OC
O- O P O CH2OG
O- O P O CH2O
TOCH2 O P O-O
AOCH2 O P O-O
COCH2 O P O-O
GOCH2 O P O-O
BIO156Paradise Valley Community College#
BIO156Paradise Valley Community College#Deoxyribonucleic Acid
(DNA)Deoxyribonucleic acid (DNA)Nucleic acid polymer that carries
hereditary materialTwo nucleotide chains twisted in a double
-helixThe function of DNA is to encode inherited information about
a cells proteins and RNAs.
BIO156Paradise Valley Community College#44
The Chemistry of Life, Part 2Paradise Valley Community
College3/5/2017
Ribonucleic Acid (RNA)Ribonucleic acid (RNA)Typically
single-stranded nucleic acid polymerFunctions in protein
synthesisThe function of RNA is to interact with DNA and with other
RNAs to carry out protein synthesis.
DNATranscribed RNA
BIO156Paradise Valley Community College#45
The Chemistry of Life, Part 2Paradise Valley Community
College3/5/2017
Disorders of Carbohydrate MetabolismObesityNon-insulin dependent
diabetes mellitus (NIDDM)Cardiovascular
diseaseCancerGastrointestinal diseases other than cancerDental
cariesHypoglycemiaKetosisWhen Things go southWhat Can Happen From a
Lack of
Carbohydrates?http://healthyeating.sfgate.com/can-happen-lack-carbohydrates-5999.html
BIO156Paradise Valley Community College#Disorders of Lipid
MetabolismGaucher's disease (inherited)Tay-Sachs disease
(inherited, Ashkenazi Jews)MCAD Deficiency (inherited, only males
affected)Fabrys disease (glycolipid build-up)Niemann-Pick Disease
(cholesterol build-up)Refsums disease (nerve & retinal
damage)When Things go southDiseases Caused by
Lipidshttp://www.livestrong.com/article/198747-diseases-caused-by-lipids/
BIO156Paradise Valley Community College#Disorders of Protein
MetabolismCachexia (depletion of skeletal muscle)Marasmus (infants,
weight loss, dehydration)Kwashiorkor (older children,
starvation)Protein C and Protein C (poor clotting)Proteopathy
(major aggregating protein)Alzheimer's disease (amyloid
peptide)Cerebral -amyloid angiopathyRetinal ganglion cell
degenerationPrion diseases (multiple)When Things go southA List of
Protein Deficiency
Diseaseshttp://www.livestrong.com/article/269901-a-list-of-protein-deficiency-diseases/
BIO156Paradise Valley Community College#Disorders of Nucleic
Acid MetabolismLesch-Nyhan Syndrome (inherited,
neuropathy)Xanthinuria (inherited, low blood uric acid)Orotic
Aciduria (inherited, retardation)Hypouricemia (inherited, sever
liver damage)Von Gierkes Disease (inherited, lactic acidosis)Reyes
Syndrome (inherited, damaged mitochondria When Things go
southDiseases Due to Errors in Nucleic Acid
Metabolismhttp://www.biologydiscussion.com/acids/nucleic-acid/diseases-due-to-errors-in-nucleic-acid-metabolism/43915
BIO156Paradise Valley Community College#When Things Go
SouthPrion (partially denatured protein)A mis-folded protein
(PrP)that becomes infectiousExample:Mad Cow Disease (BSE)in
cattleExample:CJD in humansBSE: Bovine Spongiform Encephalopathy
(cattle)CJD: Creutzfeldt-Jakob Disease (humans)
Normal
MisfoldedSource: modified from case.ntu.edu.tw. 2015.
BIO156Paradise Valley Community College#
BIO156Paradise Valley Community College#50
The Chemistry of Life, Part 2Paradise Valley Community
College3/5/2017
LDLFTEKMQKTPLEKASIFSQIFFSWTKPILWKGYRQRLELSDIYQIHPGDSADNLSERLEREWDREVATSKKNPKLINALKRCFFWKFLFYGILLYLGEVTKAVQPLLLGRIIASYDRDNEHERSIAYYLAIGLCLLFVVRMLLLHPAIFGLHHIGMQMRIAMFSLIYKKTLKLSSKVLDKISTGQLVSLLSNNLNKFDEGLALAHFVWIAPLQVLLLMGLLWDLLQASAFCGLGFLIILALFQAWLGRMMMKYRDKRAGKINERLVITSQIIENIQSVKAYCWENAMEKIIETIRETELKLTRKAAYVRYFNSSAFFFSGFFVVFLSIVPHLLLDGISLRKIFTTISFSIVLRMAVTRQFPWAVQTWYDSLGVINKIQEFLQKEEYKSLEYNLTTTEVAMENVSASWDEGIGEFFEKAKLEVNGGNISNEDPSAFFSNFSLHVAPVLRNINFKIEKGQLLAIAGSTGAGKTSLLMMIMGELEPSAGKIKHSGRISFSPQVSWIMPGTIKENIVFGVSYDQYRYLSVIKACQLEEDISKFPEKDNTVLGEGGITLSGGQRARISLARAVYKDADLYLLDSPFSYLDLFTEKEIFESCVCKLMANKTRILVTSKVEQLKKADKVLILHEGSCYFYGTFSELQDQRPEFSSHLIGFDHFNAERRNSIITETLRRCSIDSDPTGVRNEVKNKSFKQVGDFSEKRKSSIINPRKSSRKFSVMQKSQPQMSGIEEEDVPAVQGERKLSLVPESDQGEASLPRSNIFNTGPTFQARRRQSVLNLMTRTSISQGSNAFATRKTSVRKMSVSSYSNSSFEVDIYNRRLSQDSILEVSEDINEEDLKECFLDDTDSPSTTTTWNTYLRFLTAHKNFIFILVFCIVIFLAEVVASSAGLWVLKSNAPVINTTSNGNGSEISDTLSVIVTHTSFYYVFYIYVGVVDSLLALGIFRGLPLVHSLISVSKVLHKKMLHAILHAPMSTFNTMRAGRILNRFSKDTAILDDILPLSIFDLTQLVLIVIGAITVVSLLEPYIFLATVPVIVAFILLRSYFLHTSQQLKQLESEARSPIFAHLITSLKGLWTLRAFGRQPYFETLFHKALNLHTANWFLYLSTLRWFQMTIEMIFVIFFIAVSFISIATSGAGEEKVGIVLTLAMNIMNTLQWAVNASIDVDSLMRSVSRIFRFIDLPVEELINENKNKEEQLSEVLIYENDYIKKTQVWPSGGQMTVKNLSANYIDGGNTVLENISFSLSPGQRVGLLGRTGSGKSTLLSAFLRLLSTQGDIQIDGVSWQTIPLQKWRKAFGVIPQKVFIFSGSIRKNLDPYGKWSDEELLKVTEEVGLKLIIDQFPGQLDFVLLDGGCVLSHGHKQLVCLARSVLSKAKILLLDEPSAHLDPITFQIIRKTLKHAFADCTVILSEHRLEAMLECQRFLVIEDNTVRQYDSIQKLVNEKSFFKQAISHSDRLKLFPLHRRNSSKRKSRPQISALQEETEEEVQDTRLWhen
Things Go South
LDL TEKPrice M P et al. J. Biol. Chem.
1996;271:25184-25191Cystic Fibrosis1,485 amino acids508
BIO156Paradise Valley Community College#MonomersSugarsFatty
AcidsAmino AcidsNucleic Acids
Polymers Carbohydrates Lipids Proteins DNA & RNAChemistry of
Life - MacromoleculesSource: Modified from online.science.psu.edu.
2017.
. . . . . . . . . .. . . . . . .. . . . .. . . .
Carbohydrate
Triglyceride
Protein
DNA
BIO156Paradise Valley Community College#
BIO156Paradise Valley Community College#