lecture 27.1

lecture 27.1 - Organic Chemistry William H. Brown...

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27- 27- 1 Organic Organic Chemistry Chemistry William H. Brown William H. Brown Christopher S. Foote Christopher S. Foote Brent L. Iverson Brent L. Iverson
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27- 27- 2 Amino Acids Amino Acids Chapter 27 Chapter 27
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27- 27- 3 Amino Acids Amino Acids Amino acid: Amino acid: a compound that contains both an amino group and a carboxyl group α α -Amino acid: -Amino acid: an amino acid in which the amino group is on the carbon adjacent to the carboxyl group although α -amino acids are commonly written in the unionized form, they are more properly written in the zwitterion zwitterion (internal salt) form RCHCOH NH 2 O RCHCO - NH 3 + O
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27- 27- 4 Chirality of Amino Acids Chirality of Amino Acids With the exception of glycine, all protein-derived amino acids have at least one stereocenter (the α -carbon) and are chiral the vast majority have the L-configuration at their α - carbon COO - CH 3 H H 3 N L-Alanine COO - CH 3 H NH 3 + D-Alanine
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27- 27- 5 Nonpolar side chains Nonpolar side chains NH 3 + COO - NH 3 + COO - NH 3 + COO - NH 3 + COO - NH 3 + COO - S NH 3 + COO - N H H COO - NH 3 + COO - N H COO - NH 3 + Alanine (Ala, A) Glycine (Gly, G) Isoleucine (I le, I ) Leucine (Leu, L) Methionine (Met, M) Phenylalanine (Phe, F) Proline (Pro, P) Tryptophan (Trp, W) Valine (Val, V)
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27- 27- 6 Polar side chains Polar side chains NH 3 + COO - H 2 N O NH 3 + COO - H 2 N O NH 3 + COO - HO NH 3 + COO - OH Asparagine (Asn, N) Glutamine (Gln, Q) Serine (Ser, S) Threonine (Thr, T)
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27- 27- 7 NH 3 + COO - - O O NH 3 + COO - - O O NH 3 + COO - HS NH 3 + COO - HO NH 3 + COO - N H H 2 N NH 2 + NH 3 + COO - N N H NH 3 + COO - H 3 N Cysteine  (Cys, C) Tyrosine  (Tyr, Y) Glutamic acid  (Glu, E) Aspartic acid  (Asp, D)
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This note was uploaded on 03/30/2008 for the course CHEM 262 taught by Professor Forbes during the Spring '08 term at UNC.

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lecture 27.1 - Organic Chemistry William H. Brown...

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