8885d_c03_079 12/23/03 10:20 AM Page 79 mac111 mac111:reb:

Nonpolar, aliphatic R groups Aromatic R groups

   
COO COO COO COO COO COO COO


H




H 3N C H H 3N C H

C H3N C H H 3N C H H 3N C H H3N C H
H 2N CH 2
H CH3 CH CH2 CH2 CH2
H 2C CH 2
CH3 CH3 C CH
Glycine Alanine Proline Valine NH
Gly, G Ala, A Pro, P Val, V
COO COO COO OH




H3N C H H3N C H H3N C H
Phenylalanine Tyrosine Tryptophan
CH2 H C CH3 CH2 Phe, F Tyr, R Trp, W
CH CH2 CH2
CH3 CH3 CH3 S Positively charged R groups
CH3 COO COO COO
Leucine Isoleucine Methionine



Leu, L Ile, I Met, M H3N C H H3N C H H3N C H
CH2 CH2 CH2

Polar, uncharged R groups CH2 CH2 C NH

CH
COO COO COO CH2 CH2



C N
H3N C H H 3N C H H3N C H CH2 NH H




CH2OH H C OH CH2 NH3 C NH2

CH3 SH NH2
Lysine Lys, K Arginine Arg, R Histidine His, H
Serine Threonine Cysteine
pKa = 10.7 pKa = 12.5 pKa = 6.1
Ser, S Thr, T Cys, C

COO  COO Negatively charged R groups

H 3N C H H 3N C H COO COO



CH2 CH2 H 3N C H H 3N C H
C CH2 CH2 CH2
H 2N O C COO CH2
H2N O COO
Asparagine Glutamine Aspartate Asp, A Glutamate Glu, D
Asn, N Gln, Q pKa pKa
= 3.9= 3.9 pKa = 4.1

FIGURE 3–5 The 20 common amino acids of proteins. The structural histidine is shown uncharged, its pKa (see Table 3–1) is such that a
formulas show the state of ionization that would predominate at pH small but significant fraction of these groups are positively charged at
7.0. The unshaded portions are those common to all the amino acids; pH 7.0.
the portions shaded in red are the R groups. Although the R group of