chapter8 RKW

chapter8 RKW - Lecture Connections 8 | Nucleotides and...

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Lecture Connections 8 | Nucleotides and Nucleic Acids © 2009 W. H. Freeman and Company
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CHAPTER 8 Nucleotides and Nucleic Acids Biological function of nucleotides and nucleic acids Structures of common nucleotides Structure of double stranded DNA Structures of ribonucleic acids Denaturation and annealing of DNA Key topics :
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Functions of Nucleotides and Nucleic Acids Nucleotide Functions: Energy for metabolism (ATP) Enzyme cofactors (NAD + ) Signal transduction (cAMP) Nucleic Acid Functions: Storage of genetic info (DNA) Transmission of genetic info (mRNA) Processing of genetic information (ribozymes) Protein synthesis (tRNA and rRNA)
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Nucleotides and Nucleosides Nucleotide = Nitrogeneous base Pentose Phosphate Nucleoside = Nitrogeneous base Pentose Nucleobase = Nitrogeneous base
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Nucleobases Derivatives of pyrimidine or purine Nitrogen-containing heteroaromatic molecules Planar or almost planar structures Absorb UV light around 250-270 nm Note numbering on next slide
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Purine Bases Adenine and guanine are found in in both RNA and DNA Also good H-bond donors and acceptors • Adenine p K a at N1 is 3.8 • Guanine p K a at N7 is 2.4 Neutral molecules at pH 7
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Pyrimidine Bases Cytosine is found in both DNA and RNA Thymine is found only in DNA Uracil is found only in RNA All are good H-bond donors and acceptors • Cytosine p K a at N3 is 4.5 • Thymine p K a at N3 is 9.5 Neutral molecules at pH 7
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Pentose in Nucleotides 2200 β -D-ribofuranose in RNA 2200 β -2’-deoxy-D-ribofuranose in DNA Different puckered conformations of the sugar ring are possible
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Phosphate group Negatively charged at neutral pH Typically attached to 5’ position Nucleic acids are built using 5’-triphosphates Nucleic acids contain one phosphate moiety per nucleotide May be attached to other positions:
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UV Absorption of Nucleobases Absorption of UV light at 250-270 nm is due to π π * electronic transitions Excited states of common nucleobases decay rapidly via radiationless transitions Effective photoprotection of genetic material No fluorescence from nucleic acids
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β- N -Glycosidic Bond In nucleotides the pentose ring is attached to the nucleobase via N -glycosidic bond . The bond is formed to the anomeric carbon of the sugar in β configuration The bond is formed to position N1 in pyrimidines to position N9 in purines This bond is quite stable toward hydrolysis, esp. in pyrimidines Bond cleavage is catalyzed by acid
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Conformation around N -Glycosidic Bond Relatively free rotation can occur around the N-glycosidic bond in free nucleotides The torsion angle about the N-glycosidic bond (N-C1') is denoted by the symbol
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This note was uploaded on 03/08/2012 for the course CHEM 481 taught by Professor Wood during the Fall '10 term at BYU.

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chapter8 RKW - Lecture Connections 8 | Nucleotides and...

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