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Nucleic Acids
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We have studied three other sets of Macromolecules:
Carbohydrates, lipids, & proteins
The 4th macromolecule used by organisms:Nucleic Acids
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Two main types: DNA (deoxyribonucleic acid) - found in the nucleusRNA (ribonucleic acid) – found all over the cell
DNA functions:•Store genetic information “blueprint”•Transfer genetic blueprint to other generations•Controls many cellular functions
RNA functions:•Carries genetic information out of nucleus•Builds proteins
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Both types are polymers The monomers are nucleotidesRNA is a single strandDNA is a double strandBoth have a helix structure
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The basic unit for DNA and RNA is a “nucleotide”
Composed of 3 parts: 1. a nitrogenous base (1 of 5 types) 2. a pentose sugar (1 of 2 types) 3. a phosphate
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Pentose SugarsDNA = deoxyribose RNA = ribose Difference is:Deoxyribose lacks an –OH at 2’ C. Note:
5th C sticks up from ring
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C atoms numbered for orientation: “Primes" distinguish them from
atoms of nitrogenous bases.
We will be referring to this number system a lot!
Particularly note the 5’ and 3’ carbons
1’-C –OH group is in a beta () configuration
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Nitrogenous bases of nucleotides • Ring structures of N & C • Plus side chains• Double rings are purines• Single rings are pyrimidines• 5 types provide variety in nucleic acids
Note where the carbonyl groups
& amines are located
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2 purine and 3 pyrimidine bases.Thymine is only in DNA
Uracil is only in RNA (but similar to thymine)
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Purines start at upper left Nitrogen
Then move counterclockwise
on 1st ring, clockwise on 2nd
Pyrimidines start at bottom, central
Nitrogen and move
clockwise
Sugars start at far right Carbon
and move clockwise
Carbon numbering comparison:
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Nucleosides and nucleotidesA nucleoside forms by
combining a nitrogenous base (A,T,C or G) with
a pentose sugar.
Purine bases: glycosidic bond is N-9 of base and C-1' of the pentose.
Pyrimidine bases: glycosidic bond is N-1 of base and C-1' of the pentose.
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Nucleotide formation
-OH group on 5’ carbon
H atom on phosphate OH group
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H2O
Nucleotide formation
Condensation reaction or Dehydration synthesis
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Nucleotide nomenclature: "5'-monophosphate" suffix – phosphate group attached to 5’ Ce.g. "adenosine 5'-monophosphate". Prefix describes the base:
purines (double ring) end in –osine pyrimidines (single ring) end in –idine
e.g. thymine = thymidineadenine = adenosine
Ribose sugar = no additional prefixdeoxyribose + adenine = deoxyadenosine
Come on!Let it roll off the tongue!
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Deoxyadenosine 5' monophosphate
Deoxythymidine 5 ' monophosphate
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Names of the Eight Nucleotides found in DNA and RNA.
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Artificial nucleotides in treating fast growing cancers: 5-Fluorouracil
Tumor cells utilize
uracil for DNA synthesis
more efficiently
than normal cells.
Fluorinated pyrimidine
inhibits DNA synthesis.
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Nucleotide monomers are linked using "phosphodiester bonds" between
the 3' C of one sugar to the 5' C of another.
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An ester (-O-) is a condensation reaction product of an alcohol (sugars are "polyalcohols")
and an acid ( PO43- is an acid).
“Diester" signifies the formation of two
ester linkages by each phosphate
H2O is a byproduct
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The phosphate groups link to the
sugars at the 3' and 5' carbons.
This is the
sugar-phosphate “backbone” of long
nucleic acids - held together by covalent bonds
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Bases are perpendicular to
the axis like the steps of a staircase