3.

1 Amino Acids

73

TABLE 31

Properties and Conventions Associated with the Common Amino Acids Found in Proteins
pK Abbreviation/
1 Hydropathy Amino acid a

values pK Mr* R (?COOH)

Occurren ce in proteins
7 . 7 . 5.2 6 . 9 . 5 . 2 . 3 . 3 . 1 . 6 . 5 . 1 . 4 . 4 . 5 . 2 . 5 . 5 . 6 .

pK

Nonpolar, aliphatic R groups Alanine Proline Valine Leucine Isoleucine Methionine Aromat ic R groups T rosine Tr "to"han Polar, uncharged R groups Threonine $ steine% As"ara&ine (luta)ine Positively charged R groups +isti,ine Ar&inine Negatively charged R groups (luta)ate
*Mr

pK2 symbol

Ala A Pro P Val V Leu L Ile I Met M

89 115 117 131 131 149

2.34 1.99 2.32 2.36 2.36 2.28

9.69 10.96 9.62 9.60 9.68 9.21

6.01 6.48 5.97 5.98 6.02 5.74

1.8 1.6 4.2 3.8 4.5 1.9

T r ! Tr" #

181 204

2.20 2.38

9.11 9.39

10.07

5.66 5.89

-1.3 -0.9

Thr T

119

2.11

9.62

5.87

-0.7

$ s$
Asn ' (ln *

121
132 146

1.96
2.02 2.17

10.28
8.80 9.13

8.18

5.07
5.41 5.65

2.5
-3.5 -3.5

+is + Ar& -

155 174

1.82 2.17

9.17 9.04

6.00 12.48

7.59 10.76

-3.2 -4.5

(lu .

147

2.19

9.67

4.25

3.22

-3.5

values re?ect the structures as shown in Figure 35. The elements of water (M 18) are deleted when the amino acid is incor orated into a ol! e tide.
r

"# scale com$ining h!dro ho$icit! and h!dro hilicit! of % grou s. The values re?ect the free energ! ( ?G) of transfer of the amino acid side chain from a h!dro ho$ic solvent to water. This transfer is favora$le ( ?G < &' negative value in the inde() for charged or olar amino acid side chains) and unfavora$le ( ?G > &' ositive value in the inde() for amino acids with non olar or more h!dro ho$ic side chains. *ee +ha ter 11. From ,!te) -. . /oolittle) %.F. (1081) # sim le method for dis la!ing the h!dro athic character of a rotein. J. Mol. Biol. 157, 1&5131. 2#verage occurrence in more than 1)15& roteins. From /oolittle) %.F. (1080) %edundancies in rotein se3uences. 4n Prediction of Protein Structure and the Principles of Protein Conformation (Fasman) 5./.) ed.)) . 500613) 7lenum 7ress) 8ew 9or:. ;+!steine is generall! classi?ed as olar des ite having a ositive h!dro ath! inde(. This re?ects the a$ilit! of the sulfh!dr!l grou to act as a wea: acid and to form a wea: h!drogen $ond with o(!gen or nitrogen.

/see 0i&. 11192. All )olecules 3ith a chiral center are also optically active4that is5 the rotate "lane6 "olari7e, li&ht /see 8o9 1122.

KEY CONVENTION: T3o con:entions are use,

to i,enti; the car<ons in an a)ino aci,4a "ractice that can <e

con;usin&. The a,,itional car<ons in an - &rou" are co))onl ,esi&nate, /35 ')5 85 s5 an, so ;orth5 "rocee,in& out ;ro) the a car<on. 0or )ost other or&anic )ole6 cules5 car<on ato)s are si)"l nu)<ere, ;ro) one en,5 &i:in& hi&hest "riorit /$612 to the car<on 3ith the su<6 stituent containin& the ato) o; hi&hest ato)ic nu)<er.