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Chapter 16 Amino Acids, Proteins, and Enzymes 1 16.3 Formation of Peptides Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Formation of Peptides 2 A peptide bond • is an amide bond • forms between the carboxyl group of one amino acid and the amino group of the next amino acid O CH3 O + || | || + H3N—CH2—C—O– + H3N—CH—C—O– O H CH3 O || | | || + H3N—CH2—C—N—CH—C—O– peptide bond Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Formation of a Dipeptide 3 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Learning Check 4 Write the dipeptide Ser-Thr. Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Solution 5 Write the dipeptide Ser-Thr. Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Naming Peptides 6 A peptide • is named with names of all amino acids in the peptide using a -yl ending for the name • is named using the full amino acid name for the amino acid at the the C terminal N Terminal C Terminal Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Learning Check 7 Write the names and three-letter abbreviations of the tripeptides that could form from two glycines and one alanine. Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Solution 8 Write the names and three-letter abbreviations of the tripeptides that could form from two glycines and one alanine. Glycylglycylalanine Gly-Gly-Ala Glycylalanylglycine Gly-Ala-Gly Alanylglycylglycine Ala-Gly-Gly Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Learning Check 9 What are the possible tripeptides formed from one each of leucine, glycine, and alanine? Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Solution 10 Tripeptides possible from one each of leucine, glycine, and alanine: Leu-Gly-Ala Leu-Ala-Gly Ala-Leu-Gly Ala-Gly-Leu Gly-Ala-Leu Gly-Leu-Ala Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Learning Check 11 Write the three-letter abbreviation and name for the following tetrapeptide. CH3 CH3 CH–CH3 SH S CH2 CH3 O H CH O H CH2 O H CH2 O + H3N–CH–C–N–CH–C–N–CH–C–N–CH–C–O– Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Solution 12 Ala-Leu-Cys-Met Alanylleucylcysteinylmethionine CH3 CH3 CH–CH3 SH S CH2 CH3 O H CH O H CH2 O H CH2 O + H3N–CH–C–N–CH–C–N–CH–C–N–CH–C–O– Alanine Leucine Cysteine Methionine Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.
