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7) Introduction to Nucleotides and Nucleic Acidsbrandt/Chem330/Nucleotides&Nucleic... · 2015. 9....

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Introduction to Nucleotides and Nucleic Acids N N N N N N 1 2 3 4 5 6 7 8 9 1 2 3 4 5 6 Purine Pyrimidine O OH HO CH 2 HO Base Nucleoside Nucleotide Monophosphate 2´-Deoxyribonucleotide Monophosphate P O O O O O HO CH 2 Base P O O O O O OH HO CH 2 Base N N N H N NH 2 HN N N H N O H 2 N N H N O NH 2 Adenine Guanine Cytosine Thymine Uracil B a s e N u c l e o t i d e P u r i n e s P y r i m i d i n e s B a s e N u c l e o t i d e Adenosine Guanosine Cytidine Uridine Thymidine N H NH O O N H NH O O H 3 C N N N H N O HN N H N H N O O HN N H N H H N O O O HN NH O O N N N N O O CH 3 H 3 C CH 3 Hypoxanthine Xanthine Uric acid Pseudouracil 1,3,7-Trimethyl xanthine
Transcript
  • Introduction to Nucleotides and Nucleic Acids

    N

    N N

    N

    N

    N1

    2

    3

    4

    56 7

    8

    9 1

    2

    34

    5

    6

    Purine Pyrimidine

    O

    OHHO

    CH2HOBase

    2´3´

    Nucleoside

    2´3´

    NucleotideMonophosphate

    2´3´

    2´-DeoxyribonucleotideMonophosphate

    P

    O

    O

    O O O

    HO

    CH2Base

    P

    O

    O

    O O O

    OHHO

    CH2Base

    N

    N NH

    N

    NH2

    HN

    N NH

    N

    O

    H2N

    NH

    N

    O

    NH2

    Adenine

    Guanine

    Cytosine

    Thymine

    Uracil

    Base Nucleotide

    Purines Pyrimidines

    Base Nucleotide

    Adenosine

    Guanosine

    Cytidine

    Uridine

    Thymidine

    NH

    NH

    O

    O

    NH

    NH

    O

    O

    H3C

    N

    N NH

    N

    O

    HN

    NH

    NH

    N

    O

    O

    HN

    NH

    NH

    HN

    O

    O

    OHN NH

    O

    O

    N

    N N

    N

    O

    O

    CH3H3C

    CH3Hypoxanthine Xanthine Uric acid Pseudouracil 1,3,7-Trimethyl

    xanthine

  • Base-pairing

    P

    O

    O

    O O P

    O

    OO

    OHHO

    CH2O

    N

    N N

    N

    NH2

    P

    O

    O

    O

    Adenosine Triphosphate(ATP)

    O

    OHHO

    CH2O

    N

    N N

    N

    NH2

    P

    O

    O

    O

    N

    NN

    N

    NH2

    O

    OHHO

    CH2OP

    O

    O

    O

    syn anti

    NN

    NH2

    CH3

    O

    Ribose

    5-methylcytidine

    N

    N N

    N

    NHH

    Ribose

    N

    N N

    N

    NCH3H

    RiboseN6-methyladenosine

    N N

    O

    H

    CH3

    O

    Ribose

    NN

    N

    O

    Ribose

    H

    H

    N

    N N

    N

    O

    Ribose

    H

    NH

    H

    Thymidine

    Adenosine

    Cytidine

    Guanosine

  • Stereoview of A-Form DNA (from pdb ID 3V9D)

    Stereoview of B-Form DNA (from pdb ID 1A36)

  • Detecting Sequence Information in Double-stranded DNA

    Stereoview of estrogen receptor DNA-binding domain bound to DNA (from pdb ID 1HCQ)

    N

    N N

    N

    NHH

    Ribose

    N N

    O

    H

    CH3

    O

    RiboseNN

    N

    O

    Ribose

    H

    H

    N

    N N

    N

    O

    Ribose

    H

    NH

    H

    Thymidine

    Adenosine

    Cytidine

    Guanosine

    Major grooveMajor groove

    Minor grooveMinor groove

    Major groove Minor groove

  • DNA Synthesis

    O O

    O

    CH2G

    P OO

    O

    O OCH2T

    P O

    O

    O

    O OCH2C

    P O

    O

    O

    O

    OO H2CTPO

    O

    O

    OO

    O

    H2CG

    PO O

    O

    OO H2CA

    PO

    O

    O

    OO H2CC

    PO O

    AdditionalDNA

    P

    O

    O

    O O P

    O

    OO

    HO

    CH2OA

    P

    O

    O

    O

    DirectionofDNAsynthesis

    Mg2+Mg2+

    AdditionalDNA

    AdditionalDNA

  • Stereoview of Thermus thermophilus 30 S ribosome subunit (pdb ID 2wdk)

    Stereoview of Thermus thermophilus 50 S ribosome subunit (pdb ID 2wdl), with mRNA and tRNA from pdb ID 2wdk

    A site

    P site

    E site

    mRNA

    E site

    P site

    A sitemRNA

    5S rRNA

    23S rRNA

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