General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc.1 Chapter 21 Nucleic Acids and Protein Synthesis 21.1 Components of Nucleic Acids

General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc.2 Nucleic Acids Nucleic acids are  molecules that store information for cellular growth and reproduction  deoxyribonucleic acid (DNA) and ribonucleic acid (RNA)  large molecules consisting of long chains of monomers called nucleotides

General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc.3 Nucleic Acids (continued) The nucleic acids DNA and RNA are comprised of monomers called nucleotides that consist of a  base with nitrogen  pentose sugar  phosphoryl group

General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc.4 Bases The bases in DNA and RNA are  pyrimidines C, T, and U  purines A and G

General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc.5 Bases in DNA and RNA DNA contains the bases  Cytosine (C)  Guanine (G) same in both DNA and RNA  Adenine (A)  Thymine (T)different in DNA and RNA RNA contains the bases  Cytosine (C)  Guanine (G) same in both DNA and RNA  Adenine (A)  Uracil (U) different in DNA and RNA

General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc.6 Pentose Sugars The pentose (five-carbon) sugar  in RNA is ribose  in DNA is deoxyribose, with no O atom on carbon 2′  has carbon atoms numbered with primes to distinguish them from the atoms in the bases

General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc.7 A nucleoside  has a base linked by a glycosidic bond to C1′ of a sugar (ribose or deoxyribose)  is named by changing the end of the base name to osine for purines and idine for pyrimidines Nucleosides

General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc. Formation of a Nucleoside A nucleoside forms when a sugar combines with a base. 8

General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc.9 A nucleotide  has a phosphoryl group attached to the C5′ —OH group of a nucleoside  is named using the name of the nucleoside followed by -5′-monophosphate Nucleotides

General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc.10 Formation of a Nucleotide A nucleotide forms when the —OH on C5′ of a sugar in a nucleoside bonds to hydrogen phosphate. 5′5′5′5′ Phosphate and deoxycytidine Deoxycytidine monophosphate (dCMP)

General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc.11 Nucleotides of Purines

General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc.12 Nucleotides of Pyrimidines

General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc.13 Names of Nucleosides and Nucleotides

General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc.14 AMP, ADP, and ATP  Adding phosphate groups to AMP forms the diphosphate ADP and the triphosphate ATP.

General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc.15 Learning Check Give the name and abbreviation for the following molecule, and list its base and sugar.

General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc.16 Solution Give the name and abbreviation for the following molecule, and list its base and sugar. Guanosine-5’-monophosphate (GMP) Base: guanine Sugar: ribose